CN117999310A - Stabilizer formulation - Google Patents
Stabilizer formulation Download PDFInfo
- Publication number
- CN117999310A CN117999310A CN202280062531.6A CN202280062531A CN117999310A CN 117999310 A CN117999310 A CN 117999310A CN 202280062531 A CN202280062531 A CN 202280062531A CN 117999310 A CN117999310 A CN 117999310A
- Authority
- CN
- China
- Prior art keywords
- tert
- butyl
- bis
- formula
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 130
- 238000009472 formulation Methods 0.000 title description 29
- 239000003381 stabilizer Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 239000006096 absorbing agent Substances 0.000 claims abstract description 50
- 239000011368 organic material Substances 0.000 claims abstract description 35
- 230000002708 enhancing effect Effects 0.000 claims abstract description 6
- -1 polyoxymethylene Polymers 0.000 claims description 146
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 239000000654 additive Substances 0.000 claims description 17
- 239000004611 light stabiliser Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000004743 Polypropylene Substances 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 229920001155 polypropylene Polymers 0.000 claims description 13
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229920002397 thermoplastic olefin Polymers 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 8
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 7
- 235000010233 benzoic acid Nutrition 0.000 claims description 7
- 150000001559 benzoic acids Chemical class 0.000 claims description 7
- 229920000098 polyolefin Polymers 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 6
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 5
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 150000004692 metal hydroxides Chemical class 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920000573 polyethylene Polymers 0.000 claims description 5
- 229920001169 thermoplastic Polymers 0.000 claims description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000001692 EU approved anti-caking agent Substances 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 3
- 229920006324 polyoxymethylene Polymers 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- 239000005871 repellent Substances 0.000 claims description 3
- 230000002940 repellent Effects 0.000 claims description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 29
- 239000007983 Tris buffer Substances 0.000 description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 12
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 9
- 239000012964 benzotriazole Substances 0.000 description 9
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 8
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 8
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 229960001545 hydrotalcite Drugs 0.000 description 8
- 229910001701 hydrotalcite Inorganic materials 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229940116351 sebacate Drugs 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 8
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- YIMHRDBSVCPJOV-UHFFFAOYSA-N n'-(2-ethoxyphenyl)-n-(2-ethylphenyl)oxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC YIMHRDBSVCPJOV-UHFFFAOYSA-N 0.000 description 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- DBYBHKQEHCYBQV-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-dodecoxyphenol Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 DBYBHKQEHCYBQV-UHFFFAOYSA-N 0.000 description 6
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 6
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 6
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 6
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 6
- 239000002699 waste material Substances 0.000 description 6
- 229910052724 xenon Inorganic materials 0.000 description 6
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 6
- QRLSTWVLSWCGBT-UHFFFAOYSA-N 4-((4,6-bis(octylthio)-1,3,5-triazin-2-yl)amino)-2,6-di-tert-butylphenol Chemical compound CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 QRLSTWVLSWCGBT-UHFFFAOYSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 4
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 210000000988 bone and bone Anatomy 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 4
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 4
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
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- ZRPOKHXBOZQSOX-UHFFFAOYSA-N n-heptadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCC ZRPOKHXBOZQSOX-UHFFFAOYSA-N 0.000 description 1
- DBCWENWKZARTGU-UHFFFAOYSA-N n-heptadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC=[N+]([O-])CCCCCCCCCCCCCCCCC DBCWENWKZARTGU-UHFFFAOYSA-N 0.000 description 1
- WGCBLWIBXXQTAW-UHFFFAOYSA-N n-hexadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC WGCBLWIBXXQTAW-UHFFFAOYSA-N 0.000 description 1
- GCDJFNYVSDFWDB-UHFFFAOYSA-N n-hexadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC GCDJFNYVSDFWDB-UHFFFAOYSA-N 0.000 description 1
- FHAFFFSIDLDWQA-UHFFFAOYSA-N n-hexadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC=[N+]([O-])CCCCCCCCCCCCCCCC FHAFFFSIDLDWQA-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 1
- ZXGDIORKSOYRMQ-UHFFFAOYSA-N n-octadecylheptadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCC ZXGDIORKSOYRMQ-UHFFFAOYSA-N 0.000 description 1
- MCMMSXFAWOGWQE-UHFFFAOYSA-N n-octadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC MCMMSXFAWOGWQE-UHFFFAOYSA-N 0.000 description 1
- HORBOHJHQGXXOR-UHFFFAOYSA-N n-octadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCCC HORBOHJHQGXXOR-UHFFFAOYSA-N 0.000 description 1
- QXJGVICBAANVMZ-UHFFFAOYSA-N n-octyloctan-1-imine oxide Chemical compound CCCCCCCC[N+]([O-])=CCCCCCCC QXJGVICBAANVMZ-UHFFFAOYSA-N 0.000 description 1
- NYLGUNUDTDWXQE-UHFFFAOYSA-N n-phenyl-n-prop-2-enylaniline Chemical compound C=1C=CC=CC=1N(CC=C)C1=CC=CC=C1 NYLGUNUDTDWXQE-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-UHFFFAOYSA-N 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002465 nonacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000002847 sound insulator Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002983 wood substitute Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/132—Phenols containing keto groups, e.g. benzophenones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34922—Melamine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/06—Polyethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
- C08L23/12—Polypropene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Abstract
The present invention relates to a composition comprising an organic material, at least one compound having formula (a) and at least one UV absorber. Furthermore, the invention relates to an article based on organic material comprising at least one compound having formula (a) and at least one UV absorber. The invention also relates to the use of at least one compound of formula (a) and at least one UV absorber for enhancing the stability of organic materials exposed to light.
Description
Technical Field
The present invention relates to a composition comprising an organic material, at least one compound having formula (a) and at least one UV absorber. Furthermore, the invention relates to an article based on organic material comprising at least one compound having formula (a) and at least one UV absorber. The invention also relates to the use of at least one compound of formula (a) and at least one UV absorber for enhancing the stability of organic materials exposed to light.
Background
Organic materials, i.e., synthetic polymers such as polyolefins, polyethylenes, and the like, are widely used in a variety of applications because of their ease of use in the manufacture of various extruded and molded articles. However, these articles often suffer from overall instability due to repeated exposure to UV light. In order to prevent the adverse effect of UV light on articles made from organic materials, different additives are used, such as hindered amine light stabilizers, UV absorbers, etc. However, these additives or mixtures of these additives do not improve the stability of the organic material to a large extent.
It is therefore an object of the present invention to overcome the above-mentioned disadvantages and to provide a stabilizer formulation for stabilizing organic materials.
It is another object of the present invention to provide articles based on stable organic materials having a thickness of at least 300 microns.
Disclosure of Invention
Surprisingly, it has been found that the stabilizer formulation of the presently claimed invention, i.e. the combination of a UV absorber with a compound having formula (a) and an organic material, improves the durability of the final article exposed to light and thus prolongs the lifetime of the final article, thereby bringing economic value.
Accordingly, in one aspect, the presently claimed invention relates to a composition comprising:
i. an organic material;
At least one compound of formula (A)
Wherein the method comprises the steps of
E 1 is a substituted or unsubstituted C 1-C18 alkyl radical, a radical of the formula P
Wherein R, R 'and R' are independently of each other C 1-C18 alkylene,
B is an integer in the range of 1 to 3, or
A group of formula Q
Wherein T and U are each independently of the other a linear or branched C 1-C18 -alkyl radical,
E 2 is hydrogen or a hydroxyl group,
E 3、E4、E5 and E 6 are each, independently of one another, hydrogen, hydroxy, C 1-C18 alkyl, substituted or unsubstituted C 1-C18 alkoxy, phenyl, or phenyl substituted by 1,2 or 3C 1-C4 alkyl groups, or a group of the formula Q
Wherein T and U are independently of each other a linear or branched C 1-C18 alkyl group; and
At least one UV absorber.
In another aspect, the presently claimed invention relates to an organic material based article comprising:
a. At least one compound having formula (a) as defined above; and
B. at least one UV absorber.
In yet another aspect of the presently claimed invention, the presently claimed invention relates to the use of at least one compound having formula (a) and at least one UV absorber as defined above for enhancing the stability of an organic material exposed to light.
Detailed Description
Before describing the compositions and formulations of the present invention, it is to be understood that this invention is not limited to the particular compositions and formulations described, as such compositions and formulations may, of course, vary. It is also to be understood that the terminology used herein is not intended to be limiting, since the scope of the invention claimed herein will be limited only by the appended claims.
If in the following a group is defined to comprise at least a certain number of embodiments, this is meant to also comprise groups which preferably consist of only these embodiments. Furthermore, the terms "first," "second," "third" or "(a)", "(b)", "(c)", "(d)", and the like in the description and in the claims, are used for distinguishing between similar elements and not necessarily for describing a sequential or chronological order. It is to be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the invention described herein are capable of operation in other sequences than described or illustrated herein. If the terms "first", "second", "third" or "(a)", "(B)" and "(C)" or "(a)", "(B)", "(C)", "(d)", "i", "ii", etc. refer to steps of a method or use or assay, there is no time or interval of coherence between these steps, that is, these steps may be performed simultaneously or there may be time intervals of seconds, minutes, hours, days, weeks, months or even years between these steps, unless otherwise indicated in the applications described above or below.
In the following paragraphs, the different aspects of the invention are defined in more detail. Each aspect so defined may be combined with any one or more other aspects unless clearly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any one or more other features indicated as being preferred or advantageous.
Reference throughout this specification to "one embodiment" or "a preferred embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one embodiment of the present claimed invention. Thus, appearances of the phrases "in one embodiment" or "in a preferred embodiment" or "in another embodiment" in various places throughout this specification are not necessarily all referring to the same embodiment, but may. Furthermore, the particular features, structures, or characteristics may be combined in any suitable manner as will be apparent to those of ordinary skill in the art from this disclosure in one or more embodiments. Furthermore, while some embodiments described herein include some but not other features included in other embodiments, combinations of features of different embodiments are also intended to be within the scope of the invention and form different embodiments, as would be understood by one of ordinary skill in the art. For example, in the appended claims, any of the claimed embodiments may be used in any combination.
Furthermore, the ranges defined throughout this specification also include the endpoints, i.e., the ranges of 1 to 10 mean that both 1 and 10 are included in the range. For the avoidance of doubt, applicant has the right to obtain any equivalent in accordance with applicable law.
Certain terms are first defined to facilitate an understanding of the present disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which embodiments of the invention belong.
In one aspect, the presently claimed invention relates to a composition comprising:
i. an organic material;
At least one compound of formula (A)
Wherein the method comprises the steps of
E 1 is a substituted or unsubstituted C 1-C18 alkyl radical, a radical of the formula P
Wherein R, R 'and R' are independently of each other C 1-C18 alkylene,
B is an integer in the range of 1 to 3, or a group of formula Q
Wherein T and U are each independently of the other a linear or branched C 1-C18 -alkyl radical,
E 2 is hydrogen or a hydroxyl group,
E 3、E4、E5 and E 6 are each, independently of one another, hydrogen, hydroxy, C 1-C18 alkyl, substituted or unsubstituted C 1-C18 alkoxy, phenyl, or phenyl substituted by 1,2 or 3C 1-C4 alkyl groups, or a group of the formula Q
Wherein T and U are independently of each other a linear or branched C 1-C18 alkyl group; and
At least one UV absorber.
In an embodiment, the organic material is selected from the group consisting of: polyolefin, acrylonitrile/butadiene/styrene, polyvinyl chloride, polymethyl methacrylate, polyamide or polyoxymethylene, and mixtures thereof.
In a preferred embodiment, the polyolefin is a thermoplastic polyolefin. The thermoplastic polyolefin is a thermoplastic polyethylene or polypropylene.
A compound having the formula (a):
in an embodiment, the composition comprises at least one compound having formula (a)
In embodiments, E 1 is hydrogen, substituted or unsubstituted C 1-C8 alkyl, a group having formula (P) (wherein b is an integer ranging from 1 to 2), or a group having formula Q.
In an embodiment, when b is 1 then E1 is hydrogen, substituted or unsubstituted C 1-C8 alkyl, or a group of formula Q, and when b is 2 then E 1 is a group of formula P.
In embodiments, E 2 is hydrogen or hydroxy, and E 3、E4、E5 and E 6 are independently of each other hydrogen, hydroxy, C 1-C8 alkyl, substituted or unsubstituted C 1-C8 alkoxy, phenyl, or a group having formula Q.
Examples of alkyl having up to 18 carbon atoms are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1, 3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1, 3-tetramethylbutyl 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1, 3-trimethylhexyl, 1, 3-tetramethylpentyl, nonyl, decyl, undecyl 1-methylundecyl, dodecyl, 1,3, 5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl.
In a preferred embodiment, at least one compound having formula (A) is selected from the group consisting of formulas (A-1), (A-2), (A-3), (A-4), (A-5), (A-6) and (A-7).
Most of the compounds of formula (a) are known and can be prepared in analogy to methods known to those skilled in the art.
The compounds of formula (A) may be prepared, for example, in a manner analogous to that described in U.S. Pat. No. 3, 6,255,483.
In an embodiment, the UV absorber is selected from the group consisting of: 2- (2' -hydroxyphenyl) benzotriazoles, 2-hydroxybenzophenones, 2- (2-hydroxyphenyl) -1,3, 5-triazines, esters of substituted and unsubstituted benzoic acids, cyanoacrylates, oxanilides, benzoxazinones and mixtures thereof, in addition to the compounds having the formula (a) as defined above.
2- (2' -Hydroxyphenyl) benzotriazole is selected from the group consisting of: 2- (2 ' -hydroxy-5 ' -methylphenyl) -benzotriazole, 2- (3 ',5' -di-tert-butyl-2 ' -hydroxyphenyl) benzotriazole, 2- (5 ' -tert-butyl-2 ' -hydroxyphenyl) benzotriazole, 2- (2 ' -hydroxy-5 ' - (1, 3-tetramethylbutyl) phenyl) benzotriazole, 2- (3 ',5' -di-tert-butyl-2 ' -hydroxyphenyl) -5-chloro-benzotriazole, 2- (3 ' -tert-butyl-2 ' -hydroxy-5 ' -methylphenyl) -5-chloro-benzotriazole, 2- (3 ' -sec-butyl-5 ' -tert-butyl-2 ' -hydroxyphenyl) benzotriazole, 2- (2 ' -hydroxy-4 ' -octyloxyphenyl) benzotriazole, 2- (3 ',5' -di-tert-amyl-2 ' -hydroxyphenyl) benzotriazole, 2- (3 ',5' -bis- (α, α -dimethylbenzyl) -2' -hydroxyphenyl) benzotriazole, 2- (3 ' -tert-butyl-2 ' -hydroxy-5 ' - (2-octyloxycarbonyl) ethyl) -5-chloro-benzotriazole, 2- (3 '-tert-butyl-5' - [2- (2-ethylhexyloxy) -carbonylethyl ] -2 '-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3' -tert-butyl-2 '-hydroxy-5' - (2-methoxycarbonylethyl) phenyl) benzotriazole, 2- (3 '-tert-butyl-2' -hydroxy-5 '- (2-octyloxycarbonylethyl) phenyl) benzotriazole, 2- (3' -tert-butyl-5 '- [2- (2-ethylhexyloxy) carbonylethyl ] -2' -hydroxyphenyl) benzotriazole, 2- (3 '-dodecyl-2' -hydroxy-5 '-methylphenyl) benzotriazole, 2- (3' -tert-butyl-2 '-hydroxy-5' - (2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2' -methylene-bis [4- (1, 3-tetramethylbutyl) -6-benzotriazol-2-ylphenol ]; transesterification product of 2- [3' -tert-butyl-5 ' - (2-methoxycarbonylethyl) -2' -hydroxyphenyl ] -2H-benzotriazole with polyethylene glycol 300; Wherein R = 3' -tert-butyl-4 ' -hydroxy-5 ' -2H-benzotriazol-2-ylphenyl, 2- [2' -hydroxy-3 ' - (α, α -dimethylbenzyl) -5' - (1, 3-tetramethylbutyl) -phenyl ] benzotriazole, 2- [2' -hydroxy-3 ' - (1, 3-tetramethylbutyl) -5' - (α, α -dimethylbenzyl) -phenyl ] benzotriazole, and mixtures thereof.
In preferred embodiments, the 2- (2 '-hydroxyphenyl) benzotriazole is selected from the group consisting of 2- (2' -hydroxy-5 '- (1, 3-tetramethylbutyl) phenyl) benzotriazole, 2- (3' -tert-butyl-2 '-hydroxy-5' -methylphenyl) -5-chloro-benzotriazole, and mixtures thereof.
The 2-hydroxybenzophenone is selected from the group consisting of: 2-hydroxy-4-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-decyloxy-benzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4-benzyloxy-benzophenone, 2-hydroxy-4, 2',4' -trihydroxybenzophenone, 2-hydroxy-2 '-hydroxy-4, 4' -dimethoxy-benzophenone derivatives, and mixtures thereof.
In a preferred embodiment, the 2-hydroxybenzophenone is 2-hydroxy-4-octoxybenzophenone.
2- (2-Hydroxyphenyl) -1,3, 5-triazine is selected from the group consisting of: 2,4, 6-tris (2-hydroxy-4-octyloxyphenyl) -1,3, 5-triazine, 2- (2, 4-dihydroxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2, 4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4, 6-bis (4-methylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4- (2-hydroxy-3-butoxypropyloxy) phenyl ] -4, 6-bis (2, 4-dimethyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4-dodecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4-tridecyloxyphenyl ] -4, 4-dimethylphenyl ] -1,3, 5-triazine, 2- [4- (dodecyloxy/tridecyloxy-2-hydroxypropoxy) -2-hydroxyphenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4- (2-hydroxy-3-dodecyloxypropoxy) phenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-methoxyphenyl) -4, 6-diphenyl-1, 3, 5-triazine, 2,4, 6-tris [ 2-hydroxy-4- (3-butoxy-2-hydroxypropoxy) phenyl ] -1,3, 5-triazine, 2- (2-hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1, 3, 5-triazine, 2- { 2-hydroxy-4- [3- (2-ethylhexyl-1-oxy) -2-hydroxypropoxy ] phenyl } -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2, 4-bis (2-ethylhexyl-2-hydroxypropoxy) -1,3, 5-triazine, 2- (2-hydroxyphenyl) -6-phenyl ] -1,3, 5-triazine, 2- (4, 6-bis- (2, 4-dimethylphenyl) -1,3, 5-triazin-2-yl) -5- (octyloxy) -phenol, bis {2- [4- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -3-hydroxyphenoxy ] ethyl } dodecanedioic acid ester, and mixtures thereof.
In embodiments, the esters of substituted and unsubstituted benzoic acids are selected from the group consisting of: 4-tert-butyl-phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, cetyl 3, 5-di-tert-butyl-4-hydroxybenzoate, stearyl 3, 5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4, 6-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, and mixtures thereof. In a preferred embodiment, the esters of substituted and unsubstituted benzoic acids are 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate.
In an embodiment, the cyanoacrylate is selected from the group consisting of: in a preferred embodiment, the cyanoacrylate is pentaerythritol tetrakis (2-cyano-3, 3-diphenylacrylate).
In an embodiment, the oxanilide is selected from the group consisting of: 4,4 '-dioctyloxyoxanilide, 2' -diethoxyoxanilide, 2 '-dioctyloxy-5, 5' -di-tert-butyloxanilide (tert-butoxanilide), 2 '-di-dodecyloxy-5, 5' -di-tert-butyloxanilide, 2-ethoxy-2 '-ethyloxanilide, N' -bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2 '-ethyloxanilide and its mixture with 2-ethoxy-2' -ethyl-5, 4 '-di-tert-butyloxanilide, mixture of o-and p-methoxy-disubstituted oxanilides, and mixture of o-and p-ethoxy-disubstituted oxanilides, and mixtures thereof, preferably oxanilide is 2-ethoxy-2' -ethyloxanilide.
In an embodiment, the benzoxazinone is 2,2' - (1, 4-phenylene) bis [4H-3, 1-benzoxazin-4-one ].
In an embodiment, the composition further comprises at least one antioxidant, at least one metal salt of a fatty acid, at least one metal hydroxide, at least one sterically hindered amine light stabilizer, and at least one UV absorber other than those defined above.
At least one antioxidant is selected from the group consisting of: 2, 4-bis (octylmercapto) -6- (3, 5-di-tert-butyl-4-hydroxyanilino) -1,3, 5-triazine, 2-octylmercapto-4, 6-bis (3, 5-di-tert-butyl-4-hydroxyphenoxy) -1,3, 5-triazine, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxyphenoxy) -1,2, 3-triazine, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3, 5-tris (4-tert-butyl-3-hydroxy-2, 6-dimethylbenzyl) isocyanurate, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxyphenylethyl) -1,3, 5-triazine, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1, 2,3, 5-triazine, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1, 3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3, 5-tris (4-hydroxy-3, 5-hydroxybenzyl) isocyanurate, 2, 6-tris (3, 5-di-tert-butyl-4-hydroxy-4-hydroxy-3-methylbenzyl) isocyanurate 1, 4-bis (3, 5-di-tert-butyl-4-hydroxybenzyl) -2,3,5, 6-tetramethylbenzene, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) phenol, octadecyl 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, octyl-3, 5-di-tert-butyl-4-hydroxy-hydrocinnamate, hexamethylenebis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) -N- [6- [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionylamino ] hexyl ] acrylamide, bis [ monoethyl (3, 5-di-tert-butyl-4-hydroxybenzyl) phosphonate ] calcium salt, triethylene glycol bis (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, 3, 5-di-tert-butyl-4-hydroxy-hydrocinnamate, 1, 5-tris (3, 5-di-tert-butyl-4-hydroxy) cinnamate, 3-tert-butyl-4-hydroxyphenyl) -N- [6- [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionylamino ] hexyl ] acrylamide, bis [3, 5-di-tert-butyl-4-hydroxyphenyl ] methyl ] 2, 5-hydroxy-methyl-4-hydroxy-phenyl ] 2-methyl-thio-2, 3-hydroxy-methyl-4-hydroxy-ethyl-4-hydroxy-methyl-propionate, 2-methyl-2-hydroxy-methyl-4-hydroxy-methyl-2-hydroxy-methyl-ethyl propionate 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, 4- ((4, 6-bis (octylthio) -1,3, 5-triazin-2-yl) amino) -2, 6-di-tert-butylphenol, bis (1, 2, 6-pentamethyl-4-piperidinyl) [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] butylmalonate, alpha-tocopherol, 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) -N '- [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] propionyl hydrazine, tris (4-tert-butyl-3-hydroxy-2, 6-dimethylbenzyl) isocyanurate, ethylenebis [3, 3-bis [3- (1, 1-dimethylethyl) -4-hydroxyphenyl ] butyrate ], benzyl-2-acetamido-2-deoxy-alpha-D-galactoside, 2' -methylene-bis- [ 4-hydroxy-ethyl ] -2- (1, 5-dimethyl-ethyl) -2- [ 2-dimethyl-ethyl ] -2- (1, 6-dimethyl-propyl) -2- [ 2-methylphenyl ] propionyl ] isocyanurate, tris [ 2-tert-butyl-4- (5-tert-butyl-4-hydroxy-2-methylphenyl) sulfanyl-5-methylphenyl ] phosphite, (1, 2-dioxoethylene) bis (iminoethylene) bis (3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate), 2, 6-bis [ [3- (1, 1-dimethylethyl) -2-hydroxy-5-methylphenyl ] octahydro-4, 7-methano-1H-indenyl ] -4-methyl-phenol, 4' -thiobis (2-tert-butyl-5-methylphenol), 4, 6-bis (octylthiomethyl) -o-cresol, bis (octadecyl) hydroxylamine, the reaction product of N-phenyl-aniline with 2, 4-trimethylpentene, di-N-octadecyl 3,3' -thiodipropionate, didodecyl 3,3' -thiodipropionate, 4' -bis (. Alpha.), α -dimethylbenzyl) diphenylamine, dimyristoyl 3,3' -thiodipropionate, dioctadecyl disulfide, N-di (C 16-C18 alkyl) hydroxylamine, and 2, 2-bis [ [3- (dodecylthio) -1-oxopropoxy ] methyl ] propane-1, 3-diylbis [3- (dodecylthio) propionate ]. In a preferred embodiment, the at least one antioxidant is selected from the group consisting of N, N-di (C 16-C18 alkyl) hydroxylamine and 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate.
At least one sterically hindered amine light stabilizer is selected from the group consisting of: bis (1-undecoxy-2, 6-tetramethyl-4-piperidinyl) carbonate, bis (2, 6-tetramethyl-4-piperidinyl) sebacate bis (2, 6-tetramethyl-4-piperidinyl) succinate, bis (1, 2, 6-pentamethyl-4-piperidinyl) sebacate bis (2, 6-tetramethyl-4-piperidinyl) succinate bis (1, 2, 6-pentamethyl-4-piperidinyl) sebacate linear or cyclic condensates of N '-bis (2, 6-tetramethyl-4-piperidinyl) hexamethylenediamine and 4-tert-octylamino-2, 6-dichloro-1, 3, 5-triazine, tris (2, 6-tetramethyl-4-piperidinyl) nitrilotriacetate tetrakis (2, 6-tetramethyl-4-piperidinyl) -1,2,3, 4-butanetetracarboxylate, 1' - (1, 2-ethanediyl) -bis (3, 5-tetramethylpiperazinone), and 4-benzoyl-2, 6-tetramethylpiperidine, 4-stearyloxy-2, 6-tetramethylpiperidine, bis (1, 2, 6-pentamethylpiperidinyl) -2-N-butyl-2- (2-hydroxy-3, 5-di-tert-butylbenzyl) malonate, 3-N-octyl-7, 9-tetramethyl-1, 3, 8-triazaspiro [4.5] decane-2, 4-dione bis (1-octyloxy-2, 6-tetramethylpiperidinyl) sebacate, bis (1-octyloxy-2, 6-tetramethylpiperidinyl) succinate, N, linear or cyclic condensates of N' -bis (2, 6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2, 6-dichloro-1, 3, 5-triazine, condensates of 2-chloro-4, 6-bis (4-N-butylamino-2, 6-tetramethylpiperidyl) -1,3, 5-triazine and 1, 2-bis (3-aminopropylamino) ethane condensate of 2-chloro-4, 6-bis- (4-N-butylamino-1, 2, 6-pentamethylpiperidinyl) -1,3, 5-triazine and 1, 2-bis (3-aminopropylamino) ethane 8-acetyl-3-dodecyl-7, 9-tetramethyl-1, 3, 8-triazaspiro [4.5] decane-2, 4-dione, 3-dodecyl-1- (2, 6-tetramethyl-4-piperidinyl) pyrrolidine-2, 5-dione, 3-dodecyl-1- (1, 2, 6-pentamethyl-4-piperidyl) pyrrolidine-2, 5-dione, a mixture of 4-hexadecyloxy-and 4-stearyloxy-2, 6-tetramethylpiperidine, N, a condensate of N' -bis (2, 6-tetramethyl-4-piperidinyl) hexamethylenediamine and 4-cyclohexylamino-2, 6-dichloro-1, 3, 5-triazine, a condensate of 1, 2-bis (3-aminopropylamino) ethane with 2,4, 6-trichloro-1, 3, 5-triazine and 4-butylamino-2, 6-tetramethylpiperidine; condensates of 1, 6-hexamethylenediamine and 2,4, 6-trichloro-1, 3, 5-triazine and N, N-dibutylamine and 4-butylamino-2, 6-tetramethylpiperidine; n- (2, 6-tetramethyl-4-piperidinyl) -N-dodecyl succinimide, N- (1, 2, 6-pentamethyl-4-piperidinyl) -N-dodecyl succinimide 2-undecyl-7, 9-tetramethyl-1-oxa-3, 8-diaza-4-oxo-spiro [4,5] decane the reaction product of 7, 9-tetramethyl-2-cycloundecyl-1-oxa-3, 8-diaza-4-oxospiro- [4,5] decane and epichlorohydrin, 1-bis (1, 2, 6-pentamethyl-4-piperidinyloxycarbonyl) -2- (4-methoxyphenyl) ethylene, N, N '-bis-formyl-N, diester of N' -bis (2, 6-tetramethyl-4-piperidyl) hexamethylenediamine, 4-methoxymethylenemalonic acid with 1,2, 6-pentamethyl-4-hydroxypiperidine reaction products of poly [ methylpropyl-3-oxy-4- (2, 6-tetramethyl-4-piperidinyl) ] siloxane, maleic anhydride-alpha-olefin copolymer with 2, 6-tetramethyl-4-aminopiperidine or 1,2, 6-pentamethyl-4-aminopiperidine, 2, 4-bis [ N- (1-cyclohexyloxy-2, 6-tetramethylpiperidin-4-yl) -N-butylamino ] -6- (2-hydroxyethyl) amino-1, 3, 5-triazine, 1- (2-hydroxy-2-methylpropyloxy) -4-octadecanoyloxy-2, 6-tetramethylpiperidine 5- (2-ethylhexanoyl) oxymethyl-3, 5-trimethyl-2-morpholone, 2, 4-bis [ (1-cyclohexyloxy-2, 6-piperidin-4-yl) butylamino ] -6-chloro-s-triazine with N, N' -bis (3-aminopropyl) ethylenediamine, 1,3, 5-tris (N-cyclohexyl-N- (2, 6-tetramethylpiperazin-3-one-4-yl) amino) -s-triazine, 1,3, 5-tris (N-cyclohexyl-N- (1, 2, 6-pentamethylpiperazin-3-one-4-yl) amino) -s-triazine, 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine, and N, N '-bis (2, 6-tetramethyl-4-piperidinyl) -N, N' -diformylhexamethylenediamine. In a preferred embodiment, the sterically hindered amine light stabilizer is 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine.
In an embodiment, the weight ratio of UV absorber to hindered amine light stabilizer is in the range of 1:1 to 1:20, preferably the weight ratio of UV absorber to hindered amine light stabilizer is in the range of 1:2 to 1:10, more preferably the weight ratio of UV absorber to hindered amine light stabilizer is in the range of 1:2 to 1:5, and most preferably the weight ratio of UV absorber to hindered amine light stabilizer is in the range of 1:3 to 1:5.
In an embodiment, the weight ratio of the compound of formula (a) to the hindered amine light stabilizer is in the range of 1:10 to 1:40, preferably the weight ratio of the compound of formula (a) to the hindered amine light stabilizer is in the range of 1:15 to 1:35, more preferably the weight ratio of the compound of formula (a) to the hindered amine light stabilizer is in the range of 1:15 to 1:30, and most preferably the weight ratio of the compound of formula (a) to the hindered amine light stabilizer is in the range of 1:20 to 1:25.
The metal salt of at least one fatty acid is selected from the group consisting of: from the series of calcium, zinc, magnesium or aluminum salts consisting of aliphatic saturated C 2-C22 -carboxylic acid esters, aliphatic olefinic C 3-C22 -carboxylic acid esters, aliphatic C 2-C22 -carboxylic acid esters substituted with at least one OH group, cyclic or bicyclic C 5-C22 -carboxylic acid esters, aromatic C 7-C22 -carboxylic acid esters, aromatic C 7-C22 -carboxylic acid esters substituted with at least one OH group, C 1-C16 -alkyl-substituted phenyl-carboxylic acid esters and phenyl-C 1-C16 -alkyl-carboxylic acid esters.
At least one metal hydroxide is selected from the group consisting of hydrotalcite and magnesium hydroxide.
In addition to those defined above, the at least one UV absorber is selected from the group consisting of: thio synergists, phosphites and phosphonites, hydroxylamines and butyric acid. In a preferred embodiment, the at least one UV absorber is poly (4-hydroxy-2, 6-tetramethyl-1-piperidineethanol-alt-1, 4-butanedioic acid).
In an embodiment, the composition further comprises at least one additive selected from the group consisting of: slip aids, anti-caking agents, thermal fillers, pigments, anti-fogging agents and water vapor repellents.
In embodiments, the weight ratio of the compound having formula (a) to the UV absorber is in the range of 50:1 to 1:50.
In a preferred embodiment, the weight ratio of the compound having formula (a) to UV absorber is in the range of 1:20 to 20:1.
In a more preferred embodiment, the weight ratio of the compound having formula (a) to UV absorber is in the range of 1:4 to 1:10.
In a most preferred embodiment, the weight ratio of the compound having formula (a) to UV absorber is in the range of 1:4 to 1:8.
In embodiments, the composition further comprises at least one compound of formula (B) having formula (I), formula (II), formula (III), and formula (IV) and mixtures thereof.
A compound (B) having the general formula (I):
Wherein the method comprises the steps of
A 1 is selected from the group consisting of linear or branched substituted or unsubstituted C 2-C18 alkylene, substituted or unsubstituted C 5-C7 cycloalkylene, and C 1-C4 alkylene bis (C 5-C7 cycloalkylene),
A 2 is independently selected from H, straight or branched substituted or unsubstituted C 1-C12 alkyl, C 1-C12 alkoxy, substituted or unsubstituted C 5-C12 cycloalkyl, and C 5-C12 cycloalkoxy,
A 3 and A 4 are independently selected from H, linear or branched substituted or unsubstituted C 1-C12 alkyl, substituted or unsubstituted C 5-C12 cycloalkyl and a group having formula (a-1),
Or alternatively
A 3 and A 4 together with the nitrogen atom to which they are bound form a 5-to 10-membered heterocyclic ring; and
A is an integer in the range of 1 to 20, and these repeating units are the same or different;
In the context of the present invention, the term alkyl as used herein refers to acyclic saturated aliphatic residues, including straight or branched chain alkyl residues.
As used herein, "branched" refers to a chain of atoms to which one or more side chains are attached. Branching occurs by replacing substituents (e.g., hydrogen atoms) with covalently bonded aliphatic moieties.
Representative examples of straight and branched unsubstituted C 1-C12 alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1, 3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, t-butyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, isodecyl, and the like 1, 3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, 2-propylheptyl, n-octyl, 2-ethylhexyl, 1, 3-trimethylhexyl, 1, 3-tetramethylpentyl n-nonyl, n-decyl, n-undecyl, iso-undecyl, 1-methylundecyl, n-dodecyl, iso-dodecyl, and 1,3, 5-hexamethylhexyl.
Representative examples of C 1-C12 alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decyloxy, undecyloxy, and dodecyloxy.
In a preferred embodiment, the alkoxy group is selected from the group consisting of: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy and octoxy. In a more preferred embodiment, the alkoxy group is propoxy.
Representative examples of C 5-C12 cycloalkyl groups are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl and cyclododecyl.
Representative examples of C 5-C12 cycloalkoxy are cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclononyloxy, cyclodecyloxy, cycloundecyloxy and cyclododecyloxy.
In a preferred embodiment, the cycloalkoxy group is cyclohexyloxy.
A preferred example of phenyl substituted with 1, 2 or 3C 1-C4 alkyl groups is 2, 4-dimethylphenyl.
Preferred C 2-C18 alkylene groups are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2-dimethyltrimethylene and hexamethylene. In a more preferred embodiment, the alkylene is hexamethylene.
An example of a C 5-C7 cycloalkylene is cyclohexylene.
An example of a C 1-C4 alkylene bis (C 5-C7 cycloalkylene) is methylenedicyclohexyl.
Examples of the groups A 3 and A 4 which form a 5-to 10-membered heterocyclic ring together with the nitrogen atom to which they are bonded are 1-pyrrolidinyl, piperidinyl, morpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl, 1-hexahydroazepinyl (1-hexahydroazepinyl), 5,5,7-trimethyl-1-homopiperazinyl, or 4,5,5,7-tetramethyl-1-homopiperazinyl, preferably morpholinyl.
In the compound (B) having the general formula (I), the end group attached to the diamino residue is, for example, hydrogen or a group having the formula:
The end groups attached to the triazine groups are, for example, groups having the formula:
or a group of the formula/>
In a preferred embodiment, a 1 is hexamethylene and a 2 is hydrogen and propoxy.
In a preferred embodiment, A 3 is butyl,
In a preferred embodiment, A 4 is butyl.
In a preferred embodiment, a is an integer in the range of 1 to 10.
A compound (B) having the general formula (II):
Wherein the method comprises the steps of
X 1 and x 2 are independently selected from C 1 to C 30 alkoxy,
In a preferred embodiment, x 1 and x 2 are independently selected from the group consisting of linear or branched unsubstituted C 1 to C 30 alkoxy groups.
Representative examples of straight or branched unsubstituted C 1 to C 30 alkoxy groups are methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecyloxy, tetradecoxy, pentadecoxy, hexadecoxy, heptadecoxy, octadecyloxy, nonadecoxy, eicosoxy, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy and triacontyloxy.
In a preferred embodiment, x 1 and x 2 are each undecyloxy.
A compound (B) having the general formula (III):
Wherein the method comprises the steps of
Y 1 is a linear or branched, substituted or unsubstituted C 3 to C 20 alkyl group,
Y2 is C 1 to C 30 alkyl; and
In a preferred embodiment, Y 1 is a linear or branched unsubstituted C 3 to C 20 alkyl.
In an embodiment, Y 1 is selected from the group consisting of: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl.
In a preferred embodiment, Y 1 is selected from propyl or dodecyl.
In a preferred embodiment, Y 2 is a linear or branched unsubstituted C 1 to C 30 alkyl.
In an embodiment, Y 2 is selected from the group consisting of: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl and triacontyl.
In a preferred embodiment, Y 2 is selected from pentadecyl or heptadecyl.
A compound (B) having the general formula (IV):
Wherein the method comprises the steps of
Y 1 is a linear or branched, substituted or unsubstituted C 3 to C 20 alkyl group,
Y 3 is independently selected from the group consisting of linear or branched, substituted or unsubstituted C 3 to C 20 alkyl and C 3 to C 20 alkylene,
X is a C 2 to C 5 alkyl group,
N is an integer in the range of 1 to 8.
In a preferred embodiment, Y 3 is selected from the group consisting of: linear or branched unsubstituted C 3 to C 20 alkyl and C 3 to C 20 alkylene.
Representative examples of alkylene groups having up to 20 carbon atoms are methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, and eicosylene.
In a preferred embodiment, Y 1 is selected from decyl.
In a preferred embodiment, Y 3 is selected from decyl or nonyl.
In a preferred embodiment, compound (B) is selected from formulas (B-1), (B-2), (B-3), (B-4), (B-5), (B-6), (B-7) and (B-8).
Wherein a is an integer in the range of 1 to 10; and
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Wherein n is 2.
The composition may additionally contain various conventional additives, such as:
1. Antioxidant agent
1.1. Alkylated monophenols, for example 2, 6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4, 6-dimethylphenol, 2, 6-di-tert-butyl-4-ethylphenol, 2, 6-di-tert-butyl-4-n-butylphenol, 2, 6-di-tert-butyl-4-isobutylphenol, 2, 6-dicyclopentyl-4-methylphenol, 2- (. Alpha. -methylcyclohexyl) -4, 6-dimethylphenol, 2, 6-dioctadecyl-4-methylphenol, 2,4, 6-tricyclohexylphenol, 2, 6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are linear or branched in the side chains, for example 2, 6-di-nonyl-4-methylphenol, 2, 4-dimethyl-6- (1 '-methylundec-1' -yl) phenol, 2, 4-dimethyl-6- (1 '-methylheptadec-1' -yl) phenol, 2, 4-dimethyl-6- (1 '-methyltridec-1' -yl) phenol and mixtures thereof.
1.2. Alkylthiomethylphenols, for example 2, 4-dioctylthiomethyl-6-tert-butylphenol, 2, 4-dioctylthiomethyl-6-methylphenol, 2, 4-dioctylthiomethyl-6-ethylphenol, 2, 6-bis-dodecylthiomethyl-4-nonylphenol.
1.3. Hydroquinones and alkylated hydroquinones, for example 2, 6-di-tert-butyl-4-methoxyphenol, 2, 5-di-tert-butylhydroquinone, 2, 5-di-tert-amylhydroquinone, 2, 6-diphenyl-4-octadecyloxyphenol, 2, 6-di-tert-butylhydroquinone, 2, 5-di-tert-butyl-4-hydroxyanisole, 3, 5-di-tert-butyl-4-hydroxyphenyl stearate, bis (3, 5-di-tert-butyl-4-hydroxyphenyl) adipate.
1.4. Tocopherols, such as alpha-tocopherol, beta-tocopherol, gamma-tocopherol, delta-tocopherol, and mixtures thereof (vitamin E).
1.5. Hydroxylated thiodiphenyl ethers, for example 2,2 '-thiobis (6-tert-butyl-4-methylphenol), 2' -thiobis (4-octylphenol), 4 '-thiobis (6-tert-butyl-3-methylphenol), 4' -thiobis (6-tert-butyl-2-methylphenol), 4 '-thiobis (3, 6-di-sec-amylphenol), 4' -bis (2, 6-dimethyl-4-hydroxyphenyl) disulfide.
1.6. An alkylene bisphenol which is used as a starting material for the catalyst, such as 2,2' -methylenebis (6-tert-butyl-4-methylphenol), 2' -methylenebis (6-tert-butyl-4-ethylphenol), 2' -methylenebis [ 4-methyl-6- (. Alpha. -methylcyclohexyl) phenol ], 2' -methylenebis (4-methyl-6-cyclohexylphenol), 2' -methylenebis (6-nonyl-4-methylphenol) 2,2' -methylenebis (4, 6-di-t-butylphenol), 2' -ethylenebis (6-t-butyl-4-isobutylphenol), 2' -methylenebis [6- (. Alpha. -methylbenzyl) -4-nonylphenol ], 2' -methylenebis [6- (. Alpha., alpha-dimethylbenzyl) -4-nonylphenol ], 4' -methylenebis (2, 6-di-t-butylphenol), 4' -methylenebis (6-t-butyl-2-methylphenol), 1-bis (5-t-butyl-4-hydroxy-2-methylphenyl) butane, 2, 6-bis (3-t-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1, 3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1-bis (5-tert-butyl-4-hydroxy-2-methyl-phenyl) -3-n-dodecylmercaptobutane, ethylene glycol bis [3, 3-bis (3 ' -tert-butyl-4 ' -hydroxyphenyl) butyrate ], bis (3-tert-butyl-4-hydroxy-5-methyl-phenyl) dicyclopentadiene bis [2- (3 ' -tert-butyl-2 ' -hydroxy-5 ' -methylbenzyl) -6-tert-butyl-4-methylphenyl ] terephthalate, 1-bis- (3, 5-dimethyl-2-hydroxyphenyl) butane, 2-bis (3, 5-di-tert-butyl-4-hydroxyphenyl) propane, 2-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -4-n-dodecylmercaptobutane, 1, 5-tetra- (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane.
O-, N-and S-benzyl compounds, for example 3,5,3',5' -tetra-tert-butyl-4, 4' -dihydroxydibenzyl ether, octadecyl-4-hydroxy-3, 5-dimethylbenzyl mercaptoacetate, tridecyl-4-hydroxy-3, 5-di-tert-butylbenzylmercaptoacetate, tris (3, 5-di-tert-butyl-4-hydroxybenzyl) amine, bis (4-tert-butyl-3-hydroxy-2, 6-dimethylbenzyl) dithioterephthalate, bis (3, 5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3, 5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate.
1.8. Hydroxybenzylated malonates, for example bis-octadecyl-2, 2-bis (3, 5-di-tert-butyl-2-hydroxybenzyl) malonate, bis-octadecyl-2- (3-tert-butyl-4-hydroxy-5-methylbenzyl) malonate, bis-dodecylmercaptoethyl-2, 2-bis (3, 5-di-tert-butyl-4-hydroxybenzyl) malonate, bis [4- (1, 3-tetramethylbutyl) phenyl ] -2, 2-bis (3, 5-di-tert-butyl-4-hydroxybenzyl) malonate.
1.9. Aromatic hydroxybenzyl compounds, for example 1, 4-bis (3, 5-di-tert-butyl-4-hydroxybenzyl) -2,3,5, 6-tetramethylbenzene, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) phenol.
1.10. Triazine compounds, for example 2, 4-bis (octylmercapto) -6- (3, 5-di-tert-butyl-4-hydroxyanilino) -1,3, 5-triazine, 2-octylmercapto-4, 6-bis (3, 5-di-tert-butyl-4-hydroxyphenoxy) -1,3, 5-triazine, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxyphenoxy) -1,2, 3-triazine, 1,3, 5-tris (4-tert-butyl-3-hydroxy-2, 6-dimethylbenzyl) isocyanurate, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxyphenylethyl) -1,3, 5-triazine, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1, 3, 5-triazine, 1,3, 5-tris (4-tert-butyl-3-hydroxy-3-hydroxybenzyl) isocyanurate.
1.11. Benzyl phosphonates such as dimethyl-2, 5-di-tert-butyl-4-hydroxybenzyl phosphonate, diethyl-3, 5-di-tert-butyl-4-hydroxybenzyl phosphonate, dioctadecyl 5-tert-butyl-4-hydroxy-3-methylbenzyl phosphonate, the calcium salt of monoethyl 3, 5-di-tert-butyl-4-hydroxybenzyl phosphonate.
1.12. Acylaminophenols, for example 4-hydroxylauranilide (4-hydroxylauranilide), 4-hydroxystearanilide, octyl N- (3, 5-di-tert-butyl-4-hydroxyphenyl) carbamate.
An ester of b- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid with: monohydric or polyhydric alcohols, for example methanol, ethanol, N-octanol, isooctanol, octadecanol, 1, 6-hexanediol, 1, 9-nonanediol, ethylene glycol, 1, 2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N' -bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane.
An ester of b- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid with: monohydric or polyhydric alcohols, for example methanol, ethanol, N-octanol, isooctanol, octadecanol, 1, 6-hexanediol, 1, 9-nonanediol, ethylene glycol, 1, 2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N' -bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane; 3, 9-bis [2- {3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy } -1, 1-dimethylethyl ] -2,4,8, 10-tetraoxaspiro [5.5] undecane.
An ester of b- (3, 5-dicyclohexyl-4-hydroxyphenyl) propionic acid with: monohydric or polyhydric alcohols, for example methanol, ethanol, octanol, octadecanol, 1, 6-hexanediol, 1, 9-nonanediol, ethylene glycol, 1, 2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N' -bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane.
Esters of 3, 5-di-tert-butyl-4-hydroxyphenylacetic acid with: monohydric or polyhydric alcohols, for example methanol, ethanol, octanol, octadecanol, 1, 6-hexanediol, 1, 9-nonanediol, ethylene glycol, 1, 2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N' -bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane.
Amides of b- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid, e.g. N, N '-bis (3, 5-di-tert-butyl-4-hydroxyphenyl propionyl) hexamethylenediamide, N' -bis (3, 5-di-tert-butyl-4-hydroxyphenyl propionyl) trimethylene diamide, N '-bis (3, 5-di-tert-butyl-4-hydroxyphenyl propionyl) hydrazide, N' -bis [2- (3- [3, 5-di-tert-butyl-4-hydroxyphenyl ] propionyloxy) ethyl ] oxamideXL-1, supplied by You Niluo Ir corporation (Uniroyal).
1.18. Ascorbic acid (vitamin C)
1.19. Aminic antioxidants, for example N, N ' -di-isopropyl-p-phenylenediamine, N ' -di-sec-butyl-p-phenylenediamine, N ' -bis (1, 4-dimethylpentyl) -p-phenylenediamine, N, N ' -bis (1-ethyl-3-methylpentyl) -p-phenylenediamine, N ' -bis (1-methylheptyl) -p-phenylenediamine, N ' -dicyclohexyl-p-phenylenediamine, N ' -diphenyl-p-phenylenediamine, N, N ' -bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N ' -phenyl-p-phenylenediamine, N- (1, 3-dimethylbutyl) -N ' -phenyl-p-phenylenediamine, N- (1-methylheptyl) -N ' -phenyl-p-phenylenediamine, N-cyclohexyl-N ' -phenyl-p-phenylenediamine, 4- (p-toluenesulfonyl) diphenylamine, N ' -dimethyl-N, N ' -di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenyl, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine (e.g., p ' -di-tert-octyldiphenylamine), 4-N-butylaminophenol, 4-butyrylaminophenol, 4-nonanylaminophenol, 4-dodecanaminophenol, 4-octadecanoylaminophenol, bis (4-methoxyphenyl) amine, 2, 6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4 '-diaminodiphenylmethane, 4' -diaminodiphenylmethane, N, N, N ', N' -tetramethyl-4, 4 '-diaminodiphenylmethane, 1, 2-bis [ (2-methylphenyl) amino ] ethane, 1, 2-bis (phenylamino) propane, (o-tolyl) biguanide, bis [4- (1', 3 '-dimethylbutyl) phenyl ] amine, tert-octylated N-phenyl-1-naphthylamine, a mixture of mono-and dialkylated tert-butyl/tert-octyldiphenylamines, a mixture of mono-and dialkylated nonyldiphenylamines, a mixture of mono-and dialkylated dodecyldiphenylamines, a mixture of mono-and dialkylated isopropyl/isohexyldiphenylamines, a mixture of mono-and dialkylated di-tert-butyl-anilines, 2, 3-di-tert-butyl-4, 3-di-N-4-octylphenothiazine, N-4-tert-octylphenothiazine, a mixture of mono-and dialkylphenothiazine, N-4-tert-octylphenothiazine, N-4-tert-butylphenoxide, 4-N-octylphenoxide, 4-di-4-N-4' -acetylaminobenz.
UV absorbers and light stabilizers
2.1. Esters of substituted and unsubstituted benzoic acids, for example 4-tert-butyl-phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3, 5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3, 5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4, 6-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate.
2.2. Acrylic esters, for example ethyl α -cyano- β, β -diphenylacrylate, isooctyl α -cyano- β, β -diphenylacrylate, methyl α -carbonylmethoxy cinnamate, methyl α -cyano- β -methyl-p-methoxy cinnamate, butyl α -cyano- β -methyl-p-methoxy cinnamate, methyl α -methoxycarbonyl-p-methoxy cinnamate, N- (β -methoxycarbonyl- β -cyanovinyl) -2-methylindoline, neopentyl tetrakis (α -cyano- β, β -diphenylacrylate.
2.3. Nickel compounds, for example nickel complexes of 2,2' -thio-bis [4- (1, 3-tetramethylbutyl) phenol ], such as 1:1 or 1:2 complexes, with or without further ligands, such as N-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, nickel salts of monoalkyl esters, for example methyl or ethyl esters, of 4-hydroxy-3, 5-di-tert-butylbenzylphosphonic acid, nickel complexes of ketoximes, for example 2-hydroxy-4-methylphenyl undecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without further ligands.
2.4. Oxamides, for example 4,4' -dioctyloxyoxanilide, 2' -diethoxyoxanilide, 2' -dioctyloxy-5, 5' -di-tert-butyloxanilide, 2' -didodecyloxy-5, 5' -di-tert-butyloxanilide, 2-ethoxy-2 ' -ethyloxanilide, N ' -bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2 ' -ethyloxanilide and its mixture with 2-ethoxy-2 ' -ethyl-5, 4' -di-tert-butyloxanilide, mixtures of o-and p-methoxy-disubstituted oxanilides and mixtures of o-and p-ethoxy-disubstituted oxanilides.
2.5.2- (2-Hydroxyphenyl) -1,3, 5-triazines, for example 2,4, 6-tris (2-hydroxy-4-octyloxyphenyl) -1,3, 5-triazine, 2- (2, 4-dihydroxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2, 4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4, 6-bis (4-methylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4- (2-hydroxy-3-butoxypropyloxyphenyl) -4, 6-bis (4-methylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4-dodecyloxyphenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4-dodecyloxypropyloxy ] -4, 4-hydroxy-3-2-dimethylphenyl ] -1,3, 5-triazine, 2- [4- (dodecyloxy/tridecyloxy-2-hydroxypropoxy) -2-hydroxyphenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4- (2-hydroxy-3-dodecyloxypropoxy) phenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-methoxyphenyl) -4, 6-diphenyl-1, 3, 5-triazine, 2,4, 6-tris [ 2-hydroxy-4- (3-butoxy-2-hydroxypropoxy) phenyl ] -1,3, 5-triazine, 2- (2-hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1, 3, 5-triazine, 2- { 2-hydroxy-4- [3- (2-ethylhexyl-1-oxy) -2-hydroxypropoxy ] phenyl } -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2, 4-bis (2-ethylhexyl-2-hydroxypropoxy) -1,3, 5-triazine.
3. Metal deactivators, for example N, N ' -diphenyloxamide, N-salicylal-N ' -salicyloyl hydrazine, N ' -bis (salicyloyl) hydrazine, N ' -bis (3, 5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1, 2, 4-triazole, bis (benzylidene) oxalyl dihydrazide, oxanilide, isophthalic acid dihydrazide, sebacoyl bisphenylhydrazide, N ' -diacetyladipoyl dihydrazide, N ' -bis (salicyloyl) oxalyl dihydrazide, N ' -bis (salicyloyl) thiopropionyl dihydrazide.
4. Phosphites and phosphonites, for example triphenyl phosphite, diphenyl alkyl phosphite, phenyl dialkyl phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris (2, 4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol diphosphite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2, 4-di-cumylphenyl) pentaerythritol diphosphite, bis (2, 6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, diisodecyl pentaerythritol diphosphite, bis (2, 4-di-tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2, 4, 6-tris (tert-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2, 4-di-tert-butylphenyl) 4,4' -biphenylene diphosphonite, 6-isooctyloxy-2, 4,8, 10-tetra-tert-butylphenyl) bis [2, 6-di-tert-butylphenyl ] bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2, 4-di-tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2, 6-di-tert-butylphenyl) pentaerythritol diphosphite, tris (4, 6-tri-tert-butylphenyl) diphosphite, g ] -1,3, 2-dioxaphosphorinane, 2' -nitrilo [ triethyltris (3, 3', 5' -tetra-tert-butyl-1, 1' -biphenyl-2, 2' -diyl) phosphite ], 2-ethylhexyl (3, 3', 5' -tetra-tert-butyl-1, 1' -biphenyl-2, 2' -diyl) phosphite ], 5-butyl-5-ethyl-2- (2, 4, 6-tri-tert-butylphenoxy) -1,3, 2-dioxaphosphorinane (dioxaphosphirane), 2, 4-bis (1, 1-dimethylpropyl) phenyl and 4- (1, 1-dimethylpropyl) phenyltriester mixed with phosphorous acid (CAS: 939402-02-5), polymer of triphenyl phosphite with alpha-hydrogen-omega-hydroxypoly [ oxy (methyl-1, 2-ethanediyl) ] C10-16-alkyl ester (CAS: 1227937-46-3), polymer of triphenyl phosphite with 1, 4-cyclohexanedimethanol and C10-16-alkyl ester (CAS: 1821217-5771).
The following phosphites are particularly preferred:
tris (2, 4-di-t-butylphenyl) phosphite [ ] 168, Ciba SPECIALTY CHEMICALS Inc.), tris (nonylphenyl) phosphite,
5. Hydroxylamine, such as N, N-dibenzylhydroxylamine, N-diethylhydroxylamine, N-dioctylhydroxylamine, N-dilaurylhydroxylamine, N-bis-tetradecylhydroxylamine, N-bis-hexadecylhydroxylamine, N, N-bis-octadecyl hydroxylamine, N-hexadecyl-N-octadecyl hydroxylamine, N-heptadecyl-N-octadecyl hydroxylamine, N-dialkyl hydroxylamine derived from hydrogenated tallow amine.
6. Nitrones, for example N-benzyl-alpha-phenylnitrone, N-ethyl-alpha-methylnitrone, N-octyl-alpha-heptylnitrone, N-lauryl-alpha-undecylnitrone, N-tetradecyl-alpha-tridecylnitrone, N-hexadecyl-alpha-pentadecylnitrone, N-octadecyl-alpha-heptadecylnitrone, N-hexadecyl-alpha-heptadecylnitrone, N-octadecyl-alpha-pentadecylnitrone, N-heptadecyl-alpha-heptadecylnitrone, N-octadecyl-alpha-hexadecylnitrone, nitrone derived from N, N-dialkylhydroxylamine derived from hydrogenated tallow amine.
7. A thiosynergist such as dilauryl thiodipropionate, dimyristyl thiodipropionate, pentaerythritol tetrakis [3- (dodecylthio) propionate ], distearyl thiodipropionate, or distearyl disulfide.
8. Peroxide scavengers, such as esters of β -thiodipropionic acid, for example lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole, or zinc salts of 2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, bis-octadecyl disulfide, pentaerythritol tetrakis (. Beta. -dodecylmercapto) propionate.
9. Polyamide stabilizers, for example copper salts in combination with iodides and/or phosphorus compounds and salts of divalent manganese.
10. Basic co-stabilizers, for example melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids (for example calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate), antimony pyrocatecholate or zinc pyrocatecholate.
11. Nucleating agents, for example inorganic substances such as talc, metal oxides such as titanium dioxide or magnesium oxide, preferably phosphates, carbonates or sulfates of alkaline earth metals; organic compounds, such as monocarboxylic or polycarboxylic acids and salts thereof, for example 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds such as ionic copolymers (ionomers). Particularly preferred are 1,3:2, 4-bis (3 ',4' -dimethylbenzylidene) sorbitol, 1,3:2, 4-di (paramethyldibenzylidene) sorbitol, and 1,3:2, 4-di (benzylidene) sorbitol.
12. Fillers and reinforcing agents, for example calcium carbonate, silicates, surface-treated silicse:Sup>A (as described for example in U.S. Pat. No. 5,2007/60,697 and U.S. Pat. No. 2009/111,918), glass fibres, glass beads, asbestos, talc, kaolin, micse:Sup>A, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and flours or fibers of other natural products, synthetic fibers.
13. Other additives, such as plasticizers, lubricants, emulsifiers, pigments, rheology additives, catalysts, flow control agents, optical brighteners, flame retardants, antistatic agents, and blowing agents.
14. Benzofuranones and indolones, for example those :U.S.4,325,863;U.S.4,338,244;U.S.5,175,312;U.S.5,216,052;U.S.5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839,EP-A-0591102;EP-A-1291384, or 3- [4- (2-acetoxyethoxy) phenyl ] -5, 7-di-tert-butylbenzofuran-2-one, 5, 7-di-tert-butyl-3- [4- (2-stearoyloxyethoxy) phenyl ] benzofuran-2-one, 3' -bis [5, 7-di-tert-butyl-3- (4- [ 2-hydroxyethoxy ] phenyl) benzofuran-2-one ], 5, 7-di-tert-butyl-3- (4-ethoxyphenyl) benzofuran-2-one, 3- (4-acetoxy-3, 5-dimethylphenyl) -5, 7-di-tert-butyl-benzofuran-2-one, 3- (3, 5-dimethyl-4-pivaloyloxyphenyl) -5, 7-di-tert-butylbenzofuran-2-one, 3- (3, 4-dimethylphenyl) -5, 7-di-tert-butylbenzofuran-2-one, 3- (2, 3-dimethylphenyl) -5, 7-di-tert-butylbenzofuran-2-one, 3- (4-acetoxy-3, 5-dimethylphenyl) -5-i-octyl-2-one, as disclosed below.
In another aspect, the presently claimed invention relates to an organic material based article comprising:
a. At least one compound having formula (a) as defined above; and
B. at least one UV absorber as defined above.
In an embodiment, the organic material is as defined above.
The organic material based article (i.e., hollow article) may be prepared using rotational molding or blow molding, wherein the organic material based article has a thickness of at least 300 micrometers.
In yet another aspect, the presently claimed invention relates to the use of at least one compound having formula (a) as defined above and at least one UV absorber as defined above for enhancing the stability of an organic material exposed to light.
The materials stabilized according to the invention can be used in a variety of forms, for example as films, fibres, tapes, moulding compositions, profiles or as binders for paints, adhesives or putties.
In more detail, the materials stabilized according to the invention can be used to prepare the following devices:
I-1) automotive applications, in particular bumpers, dashboards, batteries, front and rear liners, under-hood mouldings, hat racks, trunk liners, interior liners, airbag covers, electronic fitting (lamp) mouldings, dashboard panels, headlight glasses, dashboards, exterior liners, interior trim, automotive lamps, headlights, parking lamps, taillights, brake lamps, interior and exterior trim; a door panel; a gasoline tank; a front surface of the glass; a rear window; seat backs, exterior panels, wire insulation, profile extrusions for sealing, cladding, pillar covers, chassis parts, exhaust systems, fuel filters/filler ports, fuel pumps, fuel tanks, body side molding, convertible tops, exterior rear view mirrors, exterior trim, fasteners/fixtures, front end modules, glass, hinges, lock systems, trunk/roof racks, press/punch parts, seals, side impact protection, dampers/sound insulators, and sunroofs.
I-2) devices for aircraft, trains, motor vehicles (automobiles, motorcycles), including decorations.
I-3) devices for space applications, in particular rockets and satellites, such as reentry shields.
I-4) devices for construction and design, mining applications, sound abatement systems, street houses and shelters.
II-1) appliances, in particular washing machines, drums, ovens (microwave ovens), dishwashers, blenders and irons.
II-2) foils for condensers, refrigerators, heating devices, air conditioners, electronic packages, semiconductors, coffee machines and vacuum cleaners.
III-1) technical products, such as cogwheels (gears), sliding fittings, gaskets, screws, bolts, handles and knobs.
III-2) rotor blades, ventilators and windmill blades, solar devices, swimming pools, swimming pool covers, swimming pool liners, pond liners, closets, wardrobes, partition walls, slat walls, folding walls, roofs, shutters (e.g. roller shutter), fittings, connections between pipes, sleeves, and conveyor belts.
III-3) profiles (panes) and wall panels of any geometry.
III-4) glass substitutes, in particular extruded sheets, for glass for buildings (monolithic, double-or multi-wall), aircraft, schools, extruded sheets, window films for architectural glass, trains, transportation, sanitary products and greenhouses.
III-5) panels (walls, cut panels), extrusion coatings (photo paper, lile packaging and duct coatings), silos, wood substitutes, plastic lumber, wood composites, walls, surfaces, furniture, decorative foils, floor coverings (interior and exterior applications), floors, pavement boards and tiles.
III-6) cements, concretes, composite applications and coverings, siding and cladding, hand rails, balustrade, countertops, roofs, shingles, tiles, and tarpaulins.
IV-1) panels (walls and cut sheets), trays, artificial turf, artificial coverings for stadiums (stadiums), artificial floors for stadiums (stadiums), and belts.
V-1) general plastic films (packaging, pouring, laminating, swimming pool covers, garbage bags, wallpaper, stretch and shrink packaging, raffia, desalination films, batteries and connectors).
V-2) agricultural films (greenhouse coverings, tunnels, coverings, silage, bales), especially in the case of large quantities of applied agrochemicals.
VI-1) food packaging and wrapping (flexible and rigid), BOPP, BOPET, bottles.
VI-2) cartridges, syringes, medical applications, any shipping container, waste basket and waste bin, waste bag, waste bin, dust bin, waste bin liner, wheeled waste bin, general container, water/used water/chemicals/gas/petroleum/petrol/diesel canister; can liners, boxes, crates, battery cases, slots, pistons, and other medical devices, ophthalmic applications, diagnostic devices, and pharmaceutical blister packages.
VII-1) means for filling polymers (talc, chalk, china clay (kaolin), wollastonite, pigments, carbon black, tiO 2, mica, nanocomposites, dolomite, silica, silicates, glass, asbestos).
The presently claimed invention provides one or more of the following advantages:
1. articles prepared by using a UV absorber in combination with a compound having formula (a) and a stable organic material improve the durability of the final article exposed to light.
2. Articles having improved light exposure durability extend the life of the final article.
3. The durable utility of the final article brings economic value.
Hereinafter, specific embodiments of the presently claimed invention are described:
1. A composition comprising:
i. an organic material;
At least one compound of formula (A)
Wherein the method comprises the steps of
E 1 is a substituted or unsubstituted C 1-C18 alkyl radical, a radical of the formula P
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Wherein R, R 'and R' are independently of each other C 1-C18 alkylene,
B is an integer in the range of 1 to 3, or
A group of formula Q
Wherein T and U are each independently of the other a linear or branched C 1-C18 -alkyl radical,
E 2 is hydrogen or a hydroxyl group,
E 3、E4、E5 and E 6 are each, independently of one another, hydrogen, hydroxy, C 1-C18 alkyl, substituted or unsubstituted C 1-C18 alkoxy, phenyl, or phenyl substituted by 1,2 or 3C 1-C4 alkyl groups, or a group of the formula Q
Wherein T and U are independently of each other a linear or branched C 1-C18 alkyl group; and
At least one UV absorber.
2. The composition according to embodiment 1, wherein the organic material is selected from the group consisting of: polyolefin, acrylonitrile/butadiene/styrene, polyvinyl chloride, polymethyl methacrylate, polyamide or polyoxymethylene, and mixtures thereof.
3. The composition of embodiment 1 or 2 wherein the polyolefin is a thermoplastic polyolefin.
4. The composition according to one or more of embodiments 1-3, wherein the thermoplastic polyolefin is a thermoplastic polyethylene or polypropylene.
5. The composition of embodiment 1, wherein E 1 is hydrogen, substituted or unsubstituted C 1-C8 alkyl, a group of formula (P) (wherein b is an integer ranging from 1 to 2), or a group of formula Q, E 2 is hydrogen or hydroxy, and E 3、E4、E5 and E 6 are independently of each other hydrogen, hydroxy, C 1-C8 alkyl, substituted or unsubstituted C 1-C8 alkoxy, phenyl, or a group of formula Q.
6. The composition according to embodiment 1 or 5, wherein the at least one compound having formula (A) is selected from formulas (A-1), (A-2), (A-3), (A-4), (A-5), (A-6) and (A-7).
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7. The composition according to embodiment 1, wherein the UV absorber is selected from the group consisting of: 2- (2' -hydroxyphenyl) benzotriazole, 2-hydroxybenzophenone, 2- (2-hydroxyphenyl) -1,3, 5-triazine, esters of substituted and unsubstituted benzoic acids, cyanoacrylates, oxanilides, benzoxazinones and mixtures thereof, except for the compound having the formula (a) as defined in example 1.
8. The composition according to example 7, wherein the 2- (2' -hydroxyphenyl) benzotriazole is selected from the group consisting of: 2- (2 ' -hydroxy-5 ' -methylphenyl) -benzotriazole, 2- (3 ',5' -di-tert-butyl-2 ' -hydroxyphenyl) benzotriazole, 2- (5 ' -tert-butyl-2 ' -hydroxyphenyl) benzotriazole, 2- (2 ' -hydroxy-5 ' - (1, 3-tetramethylbutyl) phenyl) benzotriazole, 2- (3 ',5' -di-tert-butyl-2 ' -hydroxyphenyl) -5-chloro-benzotriazole, 2- (3 ' -tert-butyl-2 ' -hydroxy-5 ' -methylphenyl) -5-chloro-benzotriazole, 2- (3 ' -sec-butyl-5 ' -tert-butyl-2 ' -hydroxyphenyl) benzotriazole, 2- (2 ' -hydroxy-4 ' -octyloxyphenyl) benzotriazole, 2- (3 ',5' -di-tert-amyl-2 ' -hydroxyphenyl) benzotriazole, 2- (3 ',5' -bis- (α, α -dimethylbenzyl) -2' -hydroxyphenyl) benzotriazole, 2- (3 ' -tert-butyl-2 ' -hydroxy-5 ' - (2-octyloxycarbonyl) ethyl) -5-chloro-benzotriazole, 2- (3 '-tert-butyl-5' - [2- (2-ethylhexyloxy) -carbonylethyl ] -2 '-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3' -tert-butyl-2 '-hydroxy-5' - (2-methoxycarbonylethyl) phenyl) benzotriazole, 2- (3 '-tert-butyl-2' -hydroxy-5 '- (2-octyloxycarbonylethyl) phenyl) benzotriazole, 2- (3' -tert-butyl-5 '- [2- (2-ethylhexyloxy) carbonylethyl ] -2' -hydroxyphenyl) benzotriazole, 2- (3 '-dodecyl-2' -hydroxy-5 '-methylphenyl) benzotriazole, 2- (3' -tert-butyl-2 '-hydroxy-5' - (2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2' -methylene-bis [4- (1, 3-tetramethylbutyl) -6-benzotriazol-2-ylphenol ]; transesterification product of 2- [3' -tert-butyl-5 ' - (2-methoxycarbonylethyl) -2' -hydroxyphenyl ] -2H-benzotriazole with polyethylene glycol 300; Wherein R = 3' -tert-butyl-4 ' -hydroxy-5 ' -2H-benzotriazol-2-ylphenyl, 2- [2' -hydroxy-3 ' - (α, α -dimethylbenzyl) -5' - (1, 3-tetramethylbutyl) -phenyl ] benzotriazole, 2- [2' -hydroxy-3 ' - (1, 3-tetramethylbutyl) -5' - (α, α -dimethylbenzyl) -phenyl ] benzotriazole, and mixtures thereof.
9. The composition according to examples 7 or 8 wherein the 2- (2 '-hydroxyphenyl) benzotriazole is selected from the group consisting of 2- (2' -hydroxy-5 '- (1, 3-tetramethylbutyl) phenyl) benzotriazole, 2- (3' -tert-butyl-2 '-hydroxy-5' -methylphenyl) -5-chloro-benzotriazole, and mixtures thereof.
10. The composition of example 7, wherein the 2-hydroxybenzophenone is selected from the group consisting of: 2-hydroxy-4-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-decyloxy-benzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4-benzyloxy-benzophenone, 2-hydroxy-4, 2',4' -trihydroxybenzophenone, 2-hydroxy-2 '-hydroxy-4, 4' -dimethoxy-benzophenone derivatives, and mixtures thereof.
11. The composition of examples 7 or 10 wherein the 2-hydroxybenzophenone is 2-hydroxy-4-octoxybenzophenone.
12. The composition of example 7, wherein the 2- (2-hydroxyphenyl) -1,3, 5-triazine is selected from the group consisting of: 2,4, 6-tris (2-hydroxy-4-octyloxyphenyl) -1,3, 5-triazine, 2- (2, 4-dihydroxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2, 4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4, 6-bis (4-methylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4- (2-hydroxy-3-butoxypropyloxy) phenyl ] -4, 6-bis (2, 4-dimethyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4-dodecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4-tridecyloxyphenyl ] -4, 4-dimethylphenyl ] -1,3, 5-triazine, 2- [4- (dodecyloxy/tridecyloxy-2-hydroxypropoxy) -2-hydroxyphenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [ 2-hydroxy-4- (2-hydroxy-3-dodecyloxypropoxy) phenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-methoxyphenyl) -4, 6-diphenyl-1, 3, 5-triazine, 2,4, 6-tris [ 2-hydroxy-4- (3-butoxy-2-hydroxypropoxy) phenyl ] -1,3, 5-triazine, 2- (2-hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1, 3, 5-triazine, 2- { 2-hydroxy-4- [3- (2-ethylhexyl-1-oxy) -2-hydroxypropoxy ] phenyl } -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2, 4-bis (2-ethylhexyl-2-hydroxypropoxy) -1,3, 5-triazine, 2- (2-hydroxyphenyl) -6-phenyl ] -1,3, 5-triazine, 2- (4, 6-bis- (2, 4-dimethylphenyl) -1,3, 5-triazin-2-yl) -5- (octyloxy) -phenol, bis {2- [4- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -3-hydroxyphenoxy ] ethyl } dodecanedioic acid ester, and mixtures thereof.
13. The composition of example 7, wherein the esters of substituted and unsubstituted benzoic acids are selected from the group consisting of: 4-tert-butyl-phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, cetyl 3, 5-di-tert-butyl-4-hydroxybenzoate, stearyl 3, 5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4, 6-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, and mixtures thereof.
14. The composition of example 7, wherein the cyanoacrylate is selected from the group consisting of: ethyl α -cyano- β, β -diphenylacrylate, isooctyl α -cyano- β, β -diphenylacrylate, neopentyl tetrakis (α -cyano- β, β -diphenylacrylate), pentaerythritol tetrakis (2-cyano-3, 3-diphenylacrylate), ethyl 2-cyano-3, 3-diphenylacrylate, (2-ethylhexyl) -2-cyano-3, 3-diphenylacrylate, and mixtures thereof.
15. The composition of example 7, wherein the oxanilide is selected from the group consisting of: 4,4' -dioctyloxyoxanilide, 2' -diethoxyoxanilide, 2' -dioctyloxy-5, 5' -di-tert-butyloxanilide, 2' -di-dodecyloxy-5, 5' -di-tert-butyloxanilide, 2-ethoxy-2 ' -ethyloxanilide, N ' -bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2 ' -ethyloxanilide and its mixture with 2-ethoxy-2 ' -ethyl-5, 4' -di-tert-butyloxanilide, mixtures of o-and p-methoxy-disubstituted oxanilides, and mixtures of o-and p-ethoxy-disubstituted oxanilides, and mixtures thereof.
16. The composition of example 7 or 15 wherein the oxanilide is 2-ethoxy-2' -ethyl oxanilide.
17. The composition of example 7, wherein the benzoxazinone is 2,2' - (1, 4-phenylene) bis [4H-3, 1-benzoxazin-4-one ].
18. The composition of one or more of embodiments 1 through 17 further comprising at least one antioxidant, at least one metal salt of a fatty acid, at least one metal hydroxide, at least one sterically hindered amine light stabilizer, and at least one UV absorber other than those disclosed in embodiments 7 through 17.
19. The composition according to embodiment 18, wherein the at least one antioxidant is selected from the group consisting of: 2, 4-bis (octylmercapto) -6- (3, 5-di-tert-butyl-4-hydroxyanilino) -1,3, 5-triazine, 2-octylmercapto-4, 6-bis (3, 5-di-tert-butyl-4-hydroxyphenoxy) -1,3, 5-triazine, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxyphenoxy) -1,2, 3-triazine, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3, 5-tris (4-tert-butyl-3-hydroxy-2, 6-dimethylbenzyl) isocyanurate, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxyphenylethyl) -1,3, 5-triazine, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1, 2,3, 5-triazine, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1, 3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3, 5-tris (4-hydroxy-3, 5-hydroxybenzyl) isocyanurate, 2, 6-tris (3, 5-di-tert-butyl-4-hydroxy-4-hydroxy-3-methylbenzyl) isocyanurate 1, 4-bis (3, 5-di-tert-butyl-4-hydroxybenzyl) -2,3,5, 6-tetramethylbenzene, 2,4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) phenol, octadecyl 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, octyl-3, 5-di-tert-butyl-4-hydroxy-hydrocinnamate, hexamethylenebis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) -N- [6- [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionylamino ] hexyl ] acrylamide, bis [ monoethyl (3, 5-di-tert-butyl-4-hydroxybenzyl) phosphonate ] calcium salt, triethylene glycol bis (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, 3, 5-di-tert-butyl-4-hydroxy-hydrocinnamate, 1, 5-tris (3, 5-di-tert-butyl-4-hydroxy) cinnamate, 3-tert-butyl-4-hydroxyphenyl) -N- [6- [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionylamino ] hexyl ] acrylamide, bis [3, 5-di-tert-butyl-4-hydroxyphenyl ] methyl ] 2, 5-hydroxy-methyl-4-hydroxy-phenyl ] 2-methyl-thio-2, 3-hydroxy-methyl-4-hydroxy-ethyl-4-hydroxy-methyl-propionate, 2-methyl-2-hydroxy-methyl-4-hydroxy-methyl-2-hydroxy-methyl-ethyl propionate 3, 5-di-tert-butyl-4-hydroxybenzoic acid 2, 4-di-tert-butylphenyl ester, 4- ((4, 6-bis (octylthio) -1,3, 5-triazin-2-yl) amino) -2, 6-di-tert-butylphenol, bis (1, 2, 6-pentamethyl-4-piperidinyl) [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] butylmalonate, alpha-tocopherol, 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) -N '- [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] propionyl hydrazine, tris (4-tert-butyl-3-hydroxy-2, 6-dimethylbenzyl) isocyanurate, ethylenebis [3, 3-bis [3- (1, 1-dimethylethyl) -4-hydroxyphenyl ] butyrate ], benzyl-2-acetamido-2-deoxy-alpha-D-galactoside, 2' -methylenebis (6-tert-butyl-4-hydroxyphenyl) propionylate, mono-2-propenoic acid, 2- (1, 1-dimethylethyl) -6- [1- [3- (1, 1-dimethylethyl) -5- (1, 1-dimethylpropyl) -2-hydroxyphenyl ] ethyl ] -4- (1, 1-dimethylpropyl) phenyl ester, tris [ 2-tert-butyl-4- (5-tert-butyl-4-hydroxy-2-methylphenyl) sulfanyl-5-methylphenyl ] phosphite, (1, 2-dioxoethylene) bis (iminoethylene) bis (3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate), 2, 6-bis [ [3- (1, 1-dimethylethyl) -2-hydroxy-5-methylphenyl ] octahydro-4, 7-methano-1H-indenyl ] -4-methyl-phenol, 4' -thiobis (2-tert-butyl-5-methylphenol), 4, 6-bis (octylthiomethyl) -o-cresol, bis (octadecyl) hydroxylamine, the reaction product of N-phenyl-aniline with 2, 4-trimethylpentene, di-N-octadecyl 3,3' -thiodipropionate, didodecyl 3,3' -thiodipropionate, 4' -bis (. Alpha.), α -dimethylbenzyl) diphenylamine, dimyristoyl 3,3' -thiodipropionate, dioctadecyl disulfide, N-di (C 16-C18 alkyl) hydroxylamine, and 2, 2-bis [ [3- (dodecylthio) -1-oxopropoxy ] methyl ] propane-1, 3-diylbis [3- (dodecylthio) propionate ].
20. The composition according to embodiment 18, wherein the at least one sterically hindered amine light stabilizer is selected from the group consisting of: bis (1-undecoxy-2, 6-tetramethyl-4-piperidinyl) carbonate, bis (2, 6-tetramethyl-4-piperidinyl) sebacate bis (2, 6-tetramethyl-4-piperidinyl) succinate, bis (1, 2, 6-pentamethyl-4-piperidinyl) sebacate bis (2, 6-tetramethyl-4-piperidinyl) succinate bis (1, 2, 6-pentamethyl-4-piperidinyl) sebacate linear or cyclic condensates of N '-bis (2, 6-tetramethyl-4-piperidinyl) hexamethylenediamine and 4-tert-octylamino-2, 6-dichloro-1, 3, 5-triazine, tris (2, 6-tetramethyl-4-piperidinyl) nitrilotriacetate tetrakis (2, 6-tetramethyl-4-piperidinyl) -1,2,3, 4-butanetetracarboxylate, 1' - (1, 2-ethanediyl) -bis (3, 5-tetramethylpiperazinone), and 4-benzoyl-2, 6-tetramethylpiperidine, 4-stearyloxy-2, 6-tetramethylpiperidine, bis (1, 2, 6-pentamethylpiperidinyl) -2-N-butyl-2- (2-hydroxy-3, 5-di-tert-butylbenzyl) malonate, 3-N-octyl-7, 9-tetramethyl-1, 3, 8-triazaspiro [4.5] decane-2, 4-dione bis (1-octyloxy-2, 6-tetramethylpiperidinyl) sebacate, bis (1-octyloxy-2, 6-tetramethylpiperidinyl) succinate, N, linear or cyclic condensates of N' -bis (2, 6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2, 6-dichloro-1, 3, 5-triazine, condensates of 2-chloro-4, 6-bis (4-N-butylamino-2, 6-tetramethylpiperidyl) -1,3, 5-triazine and 1, 2-bis (3-aminopropylamino) ethane condensate of 2-chloro-4, 6-bis- (4-N-butylamino-1, 2, 6-pentamethylpiperidinyl) -1,3, 5-triazine and 1, 2-bis (3-aminopropylamino) ethane 8-acetyl-3-dodecyl-7, 9-tetramethyl-1, 3, 8-triazaspiro [4.5] decane-2, 4-dione, 3-dodecyl-1- (2, 6-tetramethyl-4-piperidinyl) pyrrolidine-2, 5-dione, 3-dodecyl-1- (1, 2, 6-pentamethyl-4-piperidyl) pyrrolidine-2, 5-dione, a mixture of 4-hexadecyloxy-and 4-stearyloxy-2, 6-tetramethylpiperidine, N, a condensate of N' -bis (2, 6-tetramethyl-4-piperidinyl) hexamethylenediamine and 4-cyclohexylamino-2, 6-dichloro-1, 3, 5-triazine, a condensate of 1, 2-bis (3-aminopropylamino) ethane and 2,4, 6-trichloro-1, 3, 5-triazine, and 4-butylamino-2, 6-tetramethylpiperidine; condensates of 1, 6-hexamethylenediamine and 2,4, 6-trichloro-1, 3, 5-triazine and N, N-dibutylamine and 4-butylamino-2, 6-tetramethylpiperidine; n- (2, 6-tetramethyl-4-piperidinyl) -N-dodecyl succinimide, N- (1, 2, 6-pentamethyl-4-piperidinyl) -N-dodecyl succinimide 2-undecyl-7, 9-tetramethyl-1-oxa-3, 8-diaza-4-oxo-spiro [4,5] decane the reaction product of 7, 9-tetramethyl-2-cycloundecyl-1-oxa-3, 8-diaza-4-oxospiro- [4,5] decane and epichlorohydrin, 1-bis (1, 2, 6-pentamethyl-4-piperidinyloxycarbonyl) -2- (4-methoxyphenyl) ethylene, N, N '-bis-formyl-N, diester of N' -bis (2, 6-tetramethyl-4-piperidyl) hexamethylenediamine, 4-methoxymethylenemalonic acid with 1,2, 6-pentamethyl-4-hydroxypiperidine reaction products of poly [ methylpropyl-3-oxy-4- (2, 6-tetramethyl-4-piperidinyl) ] siloxane, maleic anhydride-alpha-olefin copolymer with 2, 6-tetramethyl-4-aminopiperidine or 1,2, 6-pentamethyl-4-aminopiperidine, 2, 4-bis [ N- (1-cyclohexyloxy-2, 6-tetramethylpiperidin-4-yl) -N-butylamino ] -6- (2-hydroxyethyl) amino-1, 3, 5-triazine, 1- (2-hydroxy-2-methylpropyloxy) -4-octadecanoyloxy-2, 6-tetramethylpiperidine 5- (2-ethylhexanoyl) oxymethyl-3, 5-trimethyl-2-morpholone, 2, 4-bis [ (1-cyclohexyloxy-2, 6-piperidin-4-yl) butylamino ] -6-chloro-s-triazine with N, N' -bis (3-aminopropyl) ethylenediamine, 1,3, 5-tris (N-cyclohexyl-N- (2, 6-tetramethylpiperazin-3-one-4-yl) amino) -s-triazine, 1,3, 5-tris (N-cyclohexyl-N- (1, 2, 6-pentamethylpiperazin-3-one-4-yl) amino) -s-triazine, 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine, and N, N '-bis (2, 6-tetramethyl-4-piperidinyl) -N, N' -diformylhexamethylenediamine.
21. The composition according to embodiment 18, wherein the metal salt of at least one fatty acid is selected from the group consisting of: from the series of calcium, zinc, magnesium or aluminum salts consisting of aliphatic saturated C 2-C22 -carboxylic acid esters, aliphatic olefinic C 3-C22 -carboxylic acid esters, aliphatic C 2-C22 -carboxylic acid esters substituted with at least one OH group, cyclic or bicyclic C 5-C22 -carboxylic acid esters, aromatic C 7-C22 -carboxylic acid esters, aromatic C 7-C22 -carboxylic acid esters substituted with at least one OH group, C 1-C16 -alkyl-substituted phenyl-carboxylic acid esters and phenyl-C 1-C16 -alkyl-carboxylic acid esters.
22. The composition according to embodiment 18, wherein the at least one metal hydroxide is selected from the group consisting of hydrotalcite and magnesium hydroxide.
23. The composition according to embodiment 18, wherein the at least one UV absorber is selected from the group consisting of: thio synergists, phosphites and phosphonites, hydroxylamines and butyric acid.
24. The composition of embodiments 1 through 23 further comprising at least one additive selected from the group consisting of: slip aids, anti-caking agents, thermal fillers, pigments, anti-fogging agents and water vapor repellents.
25. The composition according to one or more of embodiments 1 to 24, wherein the weight ratio of the compound having formula (a) to the UV absorber is in the range of 50:1 to 1:50.
26. The composition according to one or more of embodiments 1 to 25, wherein the weight ratio of the compound having formula (a) to the UV absorber is in the range of 1:20 to 20:1.
27. The composition of one or more of embodiments 1 through 26 further comprising at least one compound of formula (B) having formula (I), formula (II), formula (III), and formula (IV)
-Compounds (B) of general formula (I)
Wherein the method comprises the steps of
A 1 is selected from the group consisting of linear or branched substituted or unsubstituted C 2-C18 alkylene, substituted or unsubstituted C 5-C7 cycloalkylene, and C 1-C4 alkylene bis (C 5-C7 cycloalkylene),
A 2 is independently selected from H, straight or branched substituted or unsubstituted C 1-C12 alkyl, C 1-C12 alkoxy, substituted or unsubstituted C 5-C12 cycloalkyl, and C 5-C12 cycloalkoxy,
A 3 and A 4 are independently selected from H, linear or branched substituted or unsubstituted C 1-C12 alkyl, substituted or unsubstituted C 5-C12 cycloalkyl and a group having formula (a-1),
Or alternatively
A 3 and A 4 together with the nitrogen atom to which they are bound form a 5-to 10-membered heterocyclic ring; and
A is an integer in the range of 1 to 20, and these repeating units are the same or different;
-compounds (B) of general formula (II)
Wherein the method comprises the steps of
X 1 and x 2 are independently selected from C 1 to C 30 alkoxy,
-Compounds (B) of general formula (III)
Wherein the method comprises the steps of
Y 1 is a linear or branched, substituted or unsubstituted C 3 to C 20 alkyl group,
Y2 is C 1 to C 30 alkyl; and
-Compounds (B) of general formula (IV)
Wherein the method comprises the steps of
Y 1 is a linear or branched, substituted or unsubstituted C 3 to C 20 alkyl group,
Y 3 is independently selected from the group consisting of linear or branched, substituted or unsubstituted C 3 to C 20 alkyl and C 3 to C 20 alkylene,
X is a C 2 to C 5 alkyl group,
N is an integer in the range of 1 to 8.
28. The composition of embodiment 29 wherein the compound having formula (B) is selected from formulas (B-1), (B-2), (B-3), (B-4), (B-5), (B-6), (B-7), and (B-8).
Wherein a is an integer in the range of 1 to 10; and
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Wherein n is 2.
29. An organic material-based article comprising:
c. at least one compound having formula (a) as defined in examples 1, 5 and 6; and
D. at least one UV absorber as defined in examples 1, 7 to 17 and 23.
30. The organic material-based article of embodiment 29, wherein the organic material is as defined in embodiments 2-4.
31. Use of at least one compound of formula (a) as defined in examples 1, 5 and 6 and at least one UV absorber as defined in examples 1, 7 to 17 and 23 for enhancing the stability of an organic material exposed to light.
The following examples illustrate the invention in more detail. All percentages and parts are by weight unless otherwise indicated.
Examples
Example a:
Additives listed in tables 1 to 6 below:
Compound (a-1):
Compound (a-2):
Compound (a-3):
Compound (a-4):
compound (a-5):
compound (C-1): 2-ethoxy-2' -ethyl oxanilide
Compound (C-2): 2- (3 ' -tert-butyl-2 ' -hydroxy-5 ' -methylphenyl) -5-chloro-benzotriazole
Compound (C-3): 2- (2 '-hydroxy-5' - (1, 3-tetramethylbutyl) phenyl) benzotriazole
Compound (C-4): 2-hydroxy-4-octoxybenzophenone
All parts and percentages are by weight unless otherwise indicated. Weight percent (wt%) is based on the entire composition without any volatiles, if not otherwise indicated.
Sample preparation:
Example 1:
The additives were dry blended with low density polyethylene (Dow DJM-3552LDPE,0.935g/cm 3, 5.5 MI) to provide a formulation. Additive content is reported in ppm by weight based on the weight of the polyethylene. Melt extruding the dry blend into pellets on a 27mm twin screw extruder from Leistritz; setting the area to 150 ℃/200 ℃/220 ℃/230 ℃/230 ℃/230 ℃ and die opening-230 ℃; screw speed 200rpm, feeder from Kagaku (K-Tron) at 120rpm. The pellets were then compression molded in a 60 mil thick, 5 x 5 inch mold. Setting the platen at 400°f; heat softening (no pressure) for 2 minutes/low pressure heating for 2 minutes/high pressure cooling for 3 minutes. Samples were cut on a die cutter using a V-shaped dog bone die. The die cut dog bone was then exposed to a xenon lamp weatherometer from Atlas, atlas for extended periods of accelerated aging-ASTM G-155-A or DIN EN ISO 4892-2 cycle-1 methods. Mechanical properties were measured after exposure using a tensile tester from Instron, instron. For rotomolding UV-X grading systems, the% elongation retention (tensile strain at break-standard,%) was measured.
Each of formulations 1 to 15 contained 300ppm of N, N-bis (C 16-C18 -alkyl) hydroxylamine, 300ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1100ppm of tris (2, 4-di-tert-butylphenyl) phosphite, 1400ppm of 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine 700ppm of poly (4-hydroxy-2, 6-tetramethyl-1-piperidineethanol-alt-1, 4-butanedioic acid), 300ppm of hydrotalcite (acid scavenger) and 300ppm of zinc stearate (acid scavenger). Formulations 16-20 additionally contained 500ppm distearyl thiodipropionate.
Formulations 21-25 contained 300ppm of N, N-bis (C 16-C18 alkyl) hydroxylamine, 300ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1100ppm of tris (2, 4-di-tert-butylphenyl) phosphite, 1400ppm of 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine 700ppm of poly (4-hydroxy-2, 6-tetramethyl-1-piperidineethanol-alt-1, 4-butanedioic acid) 200ppm of 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, 300ppm of hydrotalcite (acid scavenger) and 300ppm of zinc stearate (acid scavenger).
All formulations contained UV absorbers or UV mixtures as described in tables 1 to 4 below.
Table 1: DIN EN ISO 4892-2 mechanical Properties (% tensile Strain at break) after 10 hours of 1 cycle exposure
Name of the name | Formulation preparation | % Tensile strain at break |
1 (Control 1) | 400ppm(C-1) | 22 |
2 | 340ppm(C-1)+60ppm(A-1) | 92 |
3 | 340ppm(C-1)+60ppm(A-2) | 93 |
4 | 340ppm(C-1)+60ppm(A-3) | 54 |
5 | 340ppm(C-1)+60ppm(A-4) | 60 |
6 (Control 2) | 400ppm(C-2) | 81 |
7 | 340ppm(C-2)+60ppm(A-1) | 93 |
8 | 340ppm(C-2)+60ppm(A-2) | 91 |
9 | 340ppm(C-2)+60ppm(A-3) | 90 |
10 | 340ppm(C-2)+60ppm(A-4) | 91 |
All formulations employed 300ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate+1100 ppm of tris (2, 4-di-tert-butylphenyl) phosphite+300 ppm of N, N-bis (C 16-C18 -alkyl) hydroxylamine+1400 ppm of 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine +700ppm poly (4-hydroxy-2, 6-tetramethyl-1-piperidineethanol-alt-1, 4-butanedioic acid) +300ppm hydrotalcite +300ppm ZnSte stable
High% tensile strain at break over exposure time is required
Example 2:
injection molded plaques prepared as described in example 1
Table 2: mechanical properties (% tensile strain at break) of astm g 155-a after 10 hours exposure
Name of the name | Formulation preparation | % Tensile strain at break |
11 (Control 3) | 400ppm(C-1) | 64 |
12 | 340ppm(C-1)+60ppm(A-1) | 97 |
13 | 340ppm(C-1)+60ppm(A-2) | 92 |
14 | 340ppm(C-1)+60ppm(A-3) | 96 |
15 | 340ppm(C-1)+60ppm(A-4) | 90 |
All formulations employed 300ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate+1100 ppm of tris (2, 4-di-tert-butylphenyl) phosphite+300 ppm of N, N-bis (C 16-C18 -alkyl) hydroxylamine+1400 ppm of 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine +700ppm poly (4-hydroxy-2, 6-tetramethyl-1-piperidineethanol-alt-1, 4-butanedioic acid) +300ppm hydrotalcite +300ppm ZnSte stable
High% tensile strain at break over exposure time is required
Example 3:
injection molded plaques prepared as described in example 1. An additional 500ppm of distearyl thiodipropionate was incorporated into the base formulation. In each case, the weight percentage of thermoplastic polyolefin was adjusted to give a total of all components of 100%.
Table 3: mechanical properties (% tensile strain at break) of astm g 155-a after 10 hours exposure
Name of the name | Formulation preparation | % Tensile strain at break |
16 (Control 4) | 400ppm(C-1) | 75 |
17 | 340ppm(C-1)+60ppm(A-1) | 80 |
18 | 340ppm(C-1)+60ppm(A-2) | 78 |
19 | 340ppm(C-1)+60ppm(A-3) | 88 |
20 | 340ppm(C-1)+60ppm(A-4) | 87 |
All formulations employed 300ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate+500 ppm of distearyl thiodipropionate+1100 ppm of tris (2, 4-di-tert-butylphenyl) phosphite+300 ppm of N, N-bis (C 16-C18 -alkyl) hydroxylamine+1400 ppm of 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine +700ppm poly (4-hydroxy-2, 6-tetramethyl-1-piperidineethanol-alt-1, 4-butanedioic acid) +300ppm hydrotalcite +300ppm ZnSte stable
High% tensile strain at break over exposure time is required
Example 4:
injection molded plaques prepared as described in example 1. An additional 200ppm of Tinuvin120 was incorporated into the base formulation. In each case, the weight percentage of thermoplastic polyolefin was adjusted to give a total of all components of 100%.
Table 4: mechanical properties (% tensile strain at break) of astm g 155-a after 10 hours exposure
Name of the name | Formulation preparation | % Tensile strain at break |
21 (Control 5) | 400ppm(C-1) | 64 |
22 | 340ppm(C-1)+60ppm(A-1) | 93 |
23 | 340ppm(C-1)+60ppm(A-2) | 89 |
24 | 340ppm(C-1)+60ppm(A-3) | 82 |
25 | 340ppm(C-1)+60ppm(A-4) | 95 |
All formulations employed 300ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate+1100 ppm of tris (2, 4-di-tert-butylphenyl) phosphite+300 ppm of N, N-bis (C 16-C18 -alkyl) hydroxylamine+1400 ppm of 4-N-butyl-2-N, 4-N-bis (2, 6-tetramethylpiperidin-4-yl) -2-N- [6- [ (2, 6-tetramethylpiperidin-4-yl) amino ] hexyl ] -1,3, 5-triazine-2, 4-diamine +700ppm poly (4-hydroxy-) -2, 6-tetramethyl-1-piperidylethanol-alt-1, 4-butanedioic acid) +200ppm of 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate +300ppm of hydrotalcite +300ppm ZnSte
High% tensile strain at break over exposure time is required
Example 5:
a blend of thermoplastic polypropylene (molen HF500N from lyandellbasell, lyondellbase); melt flow rate 12g/10min (ISO 1133); density: 90kg/m 3 (ISO 1183)) stabilized with 1000ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate+1000 ppm of tris (2, 4-di-tert-butylphenyl) phosphite+1400 ppm of N, N ' -bis (2, 6-tetramethyl-4-piperidin-yl) 1, 6-hexamethylenediamine, 2,4, 6-trichloro-1, 3, 5-triazine, N-butyl-1-butylamine and N-butyl-2, 6-tetramethyl-4-piperidinamine as reactive material+0.05% of N, N ' -bis (2, 6-tetramethyl-4-piperidyl) -N, N ' -dicarboxyl hexamethylenediamine. Additional additives listed in tables 5 and 6 below were incorporated using the same method as for the above formulation. In each case, the weight percentage of thermoplastic polyolefin was adjusted to give a total of all components of 100%.
Preparation of test samples:
The above formulations were pre-mixed in a high speed mixer. This mixture was combined with the additional additives listed in tables 5 and 6 in a high speed mixer and then compounded on a ZK25E x D extruder from kolin (Collin) at 230 ℃ and then injection molded on a Allrounder Selecta 320S 500-150 injection molding machine from albogerg (Arburg) at 230 ℃.
The entire formulation was then injection molded on an HL65 injection molding machine from Engel corporation (Engel). The injection molded plaques (85 mm. Times.90 mm. Times.1 mm) were exposed to an artificial aging according to International Standard DIN EN ISO 4892-2 cycle 1 (xenon lamp with Boro S/Boro S filter, 60W/m2 at 300-400nm (equivalent to 0.51W/(m2.nm) at 340 nm), BPT 65.+ -. 2 ℃, 50.+ -. 5% relative humidity, dry bulb temperature 38.+ -. 3 ℃, light irradiation 102min, water spray 18 min) using Atlas 5000. Gray vision and Δe were measured over time after exposure. The results are shown in Table 5.
Table 5: gray-scale vision and ΔE after 110 500 hours of DIN EN ISO 4892-2 cycle
All formulations employed 1000ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate+1000 ppm of tris (2, 4-di-tert-butylphenyl) phosphite+1400 ppm of N, N ' -bis (2, 6-tetramethyl-4-piperidin-yl) 1, 6-hexamethylenediamine, 2,4, 6-trichloro-1, 3, 5-triazine, N-butyl-1-butylamine and N-butyl-2, 6-tetramethyl-4-piperidinamine +0.05% N, N ' -bis (2, 6-tetramethyl-4-piperidinyl) -N, N ' -diformylhexamethylenediamine stable gray scale vision should > =4, and the exposure period Δe should be as low as possible
Samples were cut from injection molded plaques exposed to artificial aging (DIN EN ISO 4892-2 cycle 1 (xenon lamp with Boro S/Boro S filter, 60W/m2 at 300-400nm (equivalent to 0.51W/(m2.nm) at 340 nm), BPT 65.+ -. 2 ℃, 50.+ -. 5% relative humidity, dry bulb temperature 38.+ -. 3 ℃, light irradiation 102min, water spray 18 min)) on a die cutter using a VA-type dog bone die. Mechanical properties were measured on VA-type bone stock. The results are shown in Table 6.
Table 6: time to 50% elongation at break after exposure to DIN EN ISO 4892-2 cycle 1
All formulations employed 1000ppm of 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate+1000 ppm of tris (2, 4-di-tert-butylphenyl) phosphite+1400 ppm of N, N ' -bis (2, 6-tetramethyl-4-piperidin-yl) 1, 6-hexamethylenediamine, 2,4, 6-trichloro-1, 3, 5-triazine, N-butyl-1-butylamine and N-butyl-2, 6-tetramethyl-4-piperidinamine +0.05% N, N ' -bis (2, 6-tetramethyl-4-piperidinyl) -N, N ' -diformyl hexamethylenediamine is stabilized to 50% elongation at break for as long as possible
Example B:
Additives listed in tables 7 to 11 below:
Compound (a-2):
Compound (a-3):
compound (C-1): 2-ethoxy-2' -ethyl oxanilide
Compound (C-4): 2-hydroxy-4-octoxybenzophenone
Compound (C-5): pentaerythritol tetrakis (2-cyano-3, 3-diphenylacrylate)
Compound (C-6): 3, 5-Di-tert-butyl-4-hydroxybenzoic acid 2, 4-di-tert-butylphenyl ester
All parts and percentages are by weight unless otherwise indicated. Weight percent (wt%) is based on the entire composition without any volatiles, if not otherwise indicated.
Sample preparation:
The method comprises the following steps: the additives (all in powder form) were dry blended with ground polypropylene (PP) (Moplen HP 500N, PP homopolymer for general purpose molding applications, density 900kg/m3, melt flow rate 12g/10min at 230 ℃/2.16 kg) in a high speed mixer for 2 minutes at 3000rpm to provide the formulation. The additive content is reported in% by weight based on the weight of PP.
All examples contain a base stabilizer consisting of: 0.033% pentaerythritol tetrakis (3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate) +0.067% tris (2, 4-di-tert-butylphenyl) phosphite+0.1% N, the reaction product of a polymer of N ' -bis (2, 6-tetramethyl-4-piperidinyl) -1, 6-hexanediamine and 2,4, 6-trichloro-1, 3, 5-triazine with N-butyl-1-butylamine and N-butyl-2, 6-tetramethyl-4-piperidylamine +0.1% N, N ' -bis (2, 6-tetramethyl-4-piperidinyl) -N, N ' -diformylhexamethylenediamine.
The powder blend was melt extruded into pellets in a co-rotating twin screw extruder with a screw diameter of 25mm and an aspect ratio of 42. The screw speed was 160rpm, the throughput of material was 5 kg/hour, the zone was set at 160 ℃/170 ℃/180 ℃/190 ℃/200 ℃/210 ℃/220 ℃/220 ℃ and the melt temperature was 222 ℃ +/-1 ℃. The extruder feeder was under a nitrogen atmosphere (40 ml/min). The extrudate is cooled directly in water after leaving the cylindrical extruder nozzle. The pelletization of the extrudate was carried out in air. And obtaining the material particles.
The pellets are then compression molded on a compression molding press with aluminum foil above and below. The press temperature was 230 ℃, the preheating step was set at a pressure of 1 bar for 1 minute, the pressing step was set at a pressure of 30 bar for 2 minutes, and then the cooling step (at room temperature for 1.5 minutes at 50 bar) was performed in a separate press with a cooling system. A sheet of dimensions 2mm by 160mm by 110mm was obtained. The sheet material did not adhere to the aluminum foil. The sheet was then cut into smaller sheets of dimensions 2mm by 44mm by 68 mm.
The panels were then exposed to a xenon lamp weatherometer from atlas and subjected to accelerated aging for a long period of time according to the parameter settings of ASTM G155 cycle 1 (102 min xenon lamp (irradiance at 340nm 0.35W/(m 2 nm), dry bulb temperature 42 ℃, blackboard temperature 63 ℃, relative humidity 55%) +18 min identical cycle of xenon lamp irradiation plus water spray). Measurements were taken at different times and are given in the table below in hours.
The measuring method comprises the following steps:
Surface gloss at an angle of 60 °. A black polished glass standard plate was used to set a 100 gloss unit value (GU). The results in the following tables are given in GU units with respect to the standard values. Higher gloss values are positive.
Carbonyl increment, FT-IR based on transmission mode was measured and signals at 1710cm -1 were recorded. Values are given in percent. Low values are aggressive.
Carbonyl increment, based on FT-IR in the horizontal attenuated total reflection (H-ATR) mode, zinc selenide crystals were employed. This mode is preserved due to the wider measurement area. The signal was normalized by using the absorption peak at 2917cm -1. The carbonyl group takes a maximum value in the range 1700-1750cm -1. Values are given in percent. Low values are aggressive.
Table 7: gloss (GU, gloss units, respective values given in percent) at 60℃during exposure according to ASTM G155 cycle 1
The above results show that the gloss of PP stabilized with the examples of the present invention containing (C-1) and further triazine-based UV absorbers is significantly higher.
Table 8: carbonyl increment during cycle 1 exposure according to ASTM G155 (transmission measurement).
Values are given in percent.
Name of the name | Formulation preparation | 0 Hours | 498 Hours | 1027 Hours |
Control 11 | 0.15%(C-5) | 0 | 0.10 | 0.09 |
39 | 0.125%(C-5)+0.025%(A-3) | 0 | 0.05 | 0.06 |
The above results show that the carbonyl increment of PP stabilized with the inventive examples containing (C-5) and additional triazine-based UV absorbers is significantly lower.
Table 9: carbonyl increment during cycle 1 exposure according to ASTM G155 (transmission measurement). Values are given in percent.
The above results show that the carbonyl increment of PP stabilized with the inventive examples containing at least one UV absorber ((C-4) or (C-4) + (C-6)) and an additional triazine-based UV absorber is lower.
Table 10: carbonyl increment during cycle 1 exposure according to ASTM G155 (H-ATR method measurement). Values are given in percent.
The above results show that the carbonyl increment of PP stabilized with the inventive examples containing a mixture of two UV absorbers and an additional triazine-based UV absorber is significantly lower.
Table 11: carbonyl increment during cycle 1 exposure according to ASTM G155 (H-ATR method measurement). Values are given in percent.
The above results show that the carbonyl increment of PP stabilized with the inventive examples containing (C-1) and additional triazine-based UV is significantly lower.
Claims (15)
1. A composition comprising:
i. an organic material;
At least one compound of formula (A)
Wherein the method comprises the steps of
E 1 is a substituted or unsubstituted C 1-C18 alkyl radical, a radical of the formula P
Wherein R, R 'and R' are independently of each other C 1-C18 alkylene,
B is an integer in the range of 1 to 3, or
A group of formula Q
Wherein T and U are each independently of the other a linear or branched C 1-C18 -alkyl radical,
E 2 is hydrogen or a hydroxyl group,
E 3、E4、E5 and E 6 are each, independently of one another, hydrogen, hydroxy, C 1-C18 alkyl, substituted or unsubstituted C 1-C18 alkoxy, phenyl, or phenyl substituted by 1,2 or 3C 1-C4 alkyl groups, or a group of the formula Q
Wherein T and U are independently of each other a linear or branched C 1-C18 alkyl group; and
At least one UV absorber.
2. The composition according to claim 1, wherein the organic material is selected from the group consisting of: polyolefin, acrylonitrile/butadiene/styrene, polyvinyl chloride, polymethyl methacrylate, polyamide or polyoxymethylene, and mixtures thereof.
3. Composition according to claim 1 or2, wherein the polyolefin is a thermoplastic polyolefin.
4. A composition according to one or more of claims 1 to 3, wherein the thermoplastic polyolefin is a thermoplastic polyethylene or a thermoplastic polypropylene.
5. The composition of claim 1, wherein E 1 is hydrogen, substituted or unsubstituted C 1-C8 alkyl, a group of formula (P) wherein b is an integer ranging from 1 to 2, or a group of formula Q, E 2 is hydrogen or hydroxy, and E 3、E4、E5 and E 6 are independently of each other hydrogen, hydroxy, C 1-C8 alkyl, substituted or unsubstituted C 1-C8 alkoxy, phenyl, or a group of formula Q.
6. The composition according to claim 1 or 5, wherein the at least one compound of formula (a) is selected from the group consisting of formulas (a-1), (a-2), (a-3), (a-4), (a-5), (a-6) and (a-7):
7. The composition according to claim 1, wherein the UV absorber is selected from the group consisting of: 2- (2' -hydroxyphenyl) benzotriazoles, 2-hydroxybenzophenones, 2- (2-hydroxyphenyl) -1,3, 5-triazines, esters of substituted and unsubstituted benzoic acids, cyanoacrylates, oxanilides, benzoxazinones and mixtures thereof in addition to the compounds of formula (a) as claimed in claim 1.
8. The composition according to one or more of claims 1 to 7, further comprising at least one antioxidant, at least one metal salt of a fatty acid, at least one metal hydroxide, at least one sterically hindered amine light stabilizer, and at least one UV absorber other than those as defined in claim 7.
9. The composition according to claims 1 to 8, further comprising at least one additive selected from the group consisting of: slip aids, anti-caking agents, thermal fillers, pigments, anti-fogging agents and water vapor repellents.
10. Composition according to one or more of claims 1 to 9, in which the weight ratio of the compound of formula (a) to the UV absorber is in the range 50:1 to 1:50.
11. Composition according to one or more of claims 1 to 10, in which the weight ratio of the compound of formula (a) to the UV absorber is in the range from 1:20 to 20:1.
12. The composition according to one or more of claims 1 to 11, further comprising at least one compound of formula (B) having the general formula (I), the general formula (II), the general formula (III) and the general formula (IV)
-Compounds (B) of general formula (I)
Wherein the method comprises the steps of
A 1 is selected from the group consisting of linear or branched substituted or unsubstituted C 2-C18 alkylene, substituted or unsubstituted C 5-C7 cycloalkylene, and C 1-C4 alkylene bis (C 5-C7 cycloalkylene),
A 2 is independently selected from H, straight or branched substituted or unsubstituted C 1-C12 alkyl, C 1-C12 alkoxy, substituted or unsubstituted C 5-C12 cycloalkyl, and C 5-C12 cycloalkoxy,
A 3 and A 4 are independently selected from H, linear or branched substituted or unsubstituted C 1-C12 alkyl, substituted or unsubstituted C 5-C12 cycloalkyl and a group having formula (a-1),
Or alternatively
A 3 and A 4 together with the nitrogen atom to which they are bound form a 5-to 10-membered heterocyclic ring; and
A is an integer in the range of 1 to 20, and these repeating units are the same or different;
-compounds (B) of general formula (II)
Wherein the method comprises the steps of
X 1 and x 2 are independently selected from C 1 to C 30 alkoxy,
-Compounds (B) of general formula (III)
Wherein the method comprises the steps of
Y 1 is a linear or branched, substituted or unsubstituted C 3 to C 20 alkyl group,
Y2 is C 1 to C 30 alkyl; and
-Compounds (B) of general formula (IV)
Wherein the method comprises the steps of
Y 1 is a linear or branched, substituted or unsubstituted C 3 to C 20 alkyl group,
Y 3 is independently selected from the group consisting of linear or branched, substituted or unsubstituted C 3 to C 20 alkyl and C 3 to C 20 alkylene,
X is a C 2 to C 5 alkyl group,
N is an integer in the range of 1 to 8.
13. An organic material-based article comprising:
a. At least one compound of formula (a) as defined in claims 1, 5 and 6; and
B. at least one UV absorber as defined in claims 1 and 7.
14. An article based on an organic material according to claim 13, wherein the organic material is as defined in claims 2 to 4.
15. Use of at least one compound of formula (a) as defined in claims 1, 5 and 6 and at least one UV absorber as defined in claims 1 and 7 for enhancing the stability of an organic material exposed to light.
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PCT/EP2022/075738 WO2023041690A1 (en) | 2021-09-16 | 2022-09-16 | Stabilizer formulation |
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CN (1) | CN117999310A (en) |
AU (1) | AU2022346816A1 (en) |
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GB2042562B (en) | 1979-02-05 | 1983-05-11 | Sandoz Ltd | Stabilising polymers |
US5175312A (en) | 1989-08-31 | 1992-12-29 | Ciba-Geigy Corporation | 3-phenylbenzofuran-2-ones |
TW206220B (en) | 1991-07-01 | 1993-05-21 | Ciba Geigy Ag | |
US5252643A (en) | 1991-07-01 | 1993-10-12 | Ciba-Geigy Corporation | Thiomethylated benzofuran-2-ones |
NL9300801A (en) | 1992-05-22 | 1993-12-16 | Ciba Geigy | 3- (ACYLOXYPHENYL) BENZOFURAN-2-ON AS STABILIZERS. |
TW260686B (en) | 1992-05-22 | 1995-10-21 | Ciba Geigy | |
GB2267490B (en) | 1992-05-22 | 1995-08-09 | Ciba Geigy Ag | 3-(Carboxymethoxyphenyl)benzofuran-2-one stabilisers |
MX9305489A (en) | 1992-09-23 | 1994-03-31 | Ciba Geigy Ag | 3- (DIHIDROBENZOFURAN-5-IL) BENZOFURAN-2-ONAS, STABILIZERS. |
TW255902B (en) | 1992-09-23 | 1995-09-01 | Ciba Geigy | |
US6255483B1 (en) | 1995-03-15 | 2001-07-03 | Ciba Specialty Chemicals Corporation | Biphenyl-substituted triazines |
TW593303B (en) | 2001-09-11 | 2004-06-21 | Ciba Sc Holding Ag | Stabilization of synthetic polymers |
ZA200301683B (en) * | 2002-03-04 | 2004-09-06 | Ciba Sc Holding Ag | Synergistic combinations of UV absorbers for pigmented polyolefins. |
EP1308084A1 (en) * | 2002-10-02 | 2003-05-07 | Ciba SC Holding AG | Synergistic UV absorber combination |
EP1680465A1 (en) * | 2003-11-04 | 2006-07-19 | Cytec Technology Corp. | Uv stabilizing additive composition |
KR20070004054A (en) * | 2004-04-23 | 2007-01-05 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | Dyeable polyolefin fibers and fabrics |
US7781511B2 (en) | 2005-09-12 | 2010-08-24 | Milliken & Company | Silica-containing nucleating agent compositions and methods for using such compositions in polyolefins |
US7897663B2 (en) | 2007-10-25 | 2011-03-01 | Kuo Ching Chemical Co., Ltd. | Clarifying agent composition and manufacturing method thereof |
KR102294024B1 (en) * | 2013-09-27 | 2021-08-27 | 바스프 에스이 | Polyolefin compositions for building materials |
CN114786946A (en) * | 2020-02-10 | 2022-07-22 | 巴斯夫欧洲公司 | Light stabilizer mixture |
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